CasNo: 93-53-8
Molecular Formula: C9H10O
Appearance: clear colorless liquid
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Preparation |
By alkaline condensation of acetophenone and ethyl chloroacetate; also by distillation of methylphenyl ethylene glycol in 91% yields (under atmospheric pressure). |
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Synthesis Reference(s) |
Journal of the American Chemical Society, 97, p. 5608, 1975 DOI: 10.1021/ja00852a062Organic Syntheses, Coll. Vol. 3, p. 733, 1955Tetrahedron Letters, 15, p. 3059, 1974 |
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Flammability and Explosibility |
Nonflammable |
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Trade name |
Floralozone (IFF), Florazon (Symrise). |
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Safety Profile |
: Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES. |
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Purification Methods |
It may contain up to 15% of acetophenone. Purify it via the bisulfite addition compound [Lodge & Heathcock J Am Chem Soc 109 3353 1987] and see Chapter 2 for preparation and decomposition of bisulfite adducts. [Beilstein 7 IV 695.] |
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General Description |
2-Phenylpropionaldehyde is used in perfumes for its green hyacinth odor. |
InChI:InChI=1/C9H10O/c1-8(7-10)9-5-3-2-4-6-9/h2-8H,1H3
The organometallic synthesis of rhodium ...
Four carbonyl rhodium polyether guanidin...
Chiral disphosphite ligands (PP) prepare...
A regio- and diastereoselective samarium...
A series of highly tunable furanoside di...
Rh(I) and Ir(I) cationic complexes [M(co...
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High-performance liquid chromatography (...
Supramolecular capsules can be used to c...
styrene

carbon monoxide

3-phenyl-propionaldehyde

ethylbenzene

(S)-2-phenyl-propionaldehyde

(R)-2-phenylpropanal
| Conditions | Yield |
|---|---|
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With [(2S,3S)-2,4-bis(diphenylphosphino)pentane]Pt(SnCl3)Cl; hydrogen; In toluene; at 40 ℃; for 138h; under 51714.8 Torr;
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68.7 % Chromat. 25% 6.3% |
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With hydrogen; PtCl2
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With hydrogen; bis(benzonitrile)dichloroplatinum(II); tin(ll) chloride; (2S,4S)-2,4-bis[((S)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-2-yl)oxy]pentane; In toluene; at 100 ℃; for 2h; under 76000 Torr; Title compound not separated from byproducts;
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With hydrogen; bis(benzonitrile)dichloroplatinum(II); tin(ll) chloride; (2S,4S)-2,4-bis[((S)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-2-yl)oxy]pentane; In toluene; at 17 ℃; for 70h; under 76000 Torr; Title compound not separated from byproducts;
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With chiral bis(octahydrodinaphthodioxaphosphepin)-based ligand; hydrogen; tin(ll) chloride; bis(benzonitrile)dichloroplatinum(II); In toluene; at 23 ℃; for 20h; Title compound not separated from byproducts;
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With hydrogen; [Rh(NBD)(S)-BINAPO]BF4; In toluene; at 40 ℃; for 15h; under 60004.8 Torr; Further Variations:; Catalysts; Solvents; Temperatures; Product distribution;
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With hydrogen; chiral bis(phosphite)PtCl2-SnCl2; In toluene; at 100 ℃; for 2h; under 76000 Torr; Product distribution; other temp., times, solvent and catalyst;
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With (2S,4S)-2-(dibenzophospholyl)-4-(diphenylphosphino)pentane; hydrogen; tin(ll) chloride; bis(benzonitrile)dichloroplatinum(II); In toluene; at 24 ℃; for 45h; under 148200 Torr; Further Variations:; Catalysts; Temperatures; Pressures; Kinetics; Product distribution;
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With hydrogen; tris(pentafluorophenyl)borate; In toluene; at 100 ℃; for 24h; under 60006 Torr; Title compound not separated from byproducts.;
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With C24H23Cl3P2Pt; hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 24h; under 30003 Torr; optical yield given as %ee; chemoselective reaction; Autoclave; Inert atmosphere;
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With (R(P),R(P))-cis-bis(1-propyl-3-methyl-3-phospholano)-dichloro-platinum(II); hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 96h; under 60006 Torr; optical yield given as %ee; regioselective reaction; Inert atmosphere;
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With cis-[bis(1-ethyl-3-methyl-3-phospholeno)-dichloro-platinum(II)]; hydrogen; tin(ll) chloride; In toluene; at 60 ℃; for 72h; under 60006 Torr; Reagent/catalyst; Temperature; Time; enantioselective reaction; Inert atmosphere; Autoclave;
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29 % ee |
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With PtCl2{(-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane}; hydrogen; tin(ll) chloride; In toluene; at 60 ℃; for 18h; under 60006 Torr; Temperature; enantioselective reaction; Inert atmosphere; Autoclave;
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40 % ee |
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With PtCl2{(-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane}; hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 3h; under 60006 Torr; Temperature; enantioselective reaction; Inert atmosphere; Autoclave;
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7 % ee |
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With cis-[bis((S)-1-isopropyl-3-methyl-3-phospholeno)dichloroplatinum(II)]; hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 24h; under 60006 Torr; Temperature; enantioselective reaction; Inert atmosphere; Autoclave;
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10 % ee |
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With cis-[bis((R)-4-chloro-1-phenyl-5-methyl-1,2,3,6-tetrahydrophosphinino)-dichloroplatinum(II)]; hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 10h; under 60006 Torr; Temperature; Time; chemoselective reaction; Catalytic behavior; Inert atmosphere;
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8 % ee |
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With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride; In toluene; at 40 ℃; for 120h; under 30003 Torr; Temperature; enantioselective reaction; Autoclave; Schlenk technique;
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32 % ee |
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With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride; In toluene; at 60 ℃; for 120h; under 60006 Torr; enantioselective reaction; Autoclave; Schlenk technique;
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16 % ee |
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With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 23h; under 30003 Torr; Temperature; enantioselective reaction; Autoclave; Schlenk technique;
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24 % ee |
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With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 23h; under 60006 Torr; Temperature; enantioselective reaction; Autoclave; Schlenk technique;
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24 % ee |
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With (S)-5,5 ′-bis[di(3,5-xylyl)phosphino]-4,4 ′-bi-1,3-benzodioxole; di-μ-chlorobis(norbornadiene)dirhodium(I); hydrogen; at 60 ℃; for 24h; under 60006 Torr; Autoclave; Schlenk technique;
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styrene

carbon monoxide

3-phenyl-propionaldehyde

ethylbenzene

(S)-2-phenyl-propionaldehyde
| Conditions | Yield |
|---|---|
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With hydrogen; PtCl(SnCl3)<(S,S)-BDPP>; In toluene; at 40 ℃; for 55h; under 60004.8 Torr;
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31% 3% 42% |
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With hydrogen; PtCl(SnCl3)<(S,S)-BDPP>; In toluene; at 40 ℃; for 55h;
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42% 3% 31% |
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With C44H32Cl4P2PtSn(2+); hydrogen; at 40 ℃; for 336h; under 30003 Torr; Reagent/catalyst; Solvent; Temperature; Time; Pressure; chemoselective reaction;
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49 % ee |
2-Phenylpropanal
styrene
carbon monoxide
3-phenylbut-1-ene
(2S,3R)-threo-2-phenylpentan-3-ol
(2S,3S)-erythro-2-phenylpentan-3-ol
methyl (3R,4S)-3-hydroxy-4-phenylpentanoate
Methyl-erythro-3-Hydroxy-4-phenylvalerat