Carbon Dioxide → 2-Phenylpropanal
Reaction equation
C=CC1C=CC=CC=1.CCCCCCCCCCC.C(=O)=O.C1(CCC=O)C=CC=CC=1.[C:33]1([C@@H:39]([CH3:42])[CH:40]=[O:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[C:33]1([CH:39]([CH3:42])[CH:40]=[O:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1Participants
Conditions
- Temperature
- -60 °C
Procedure
To a 300 mL stainless steel autoclave equipped with two sapphire windows containing Rh(acac)(CO)2 (10.4 mg, 4×10-2 mmol) and (R,S)-BINAPHOS (60 mg, 8×10-2 mmol) were added styrene (2.08 g, 2.0 mmol) and n-undecane (156 mg, 1.0 mmol) (the internal standard for GC analysis). The air was replaced by CO through pressurization (2-3 atm) and release for 2-3 times, and CO (7 atm) was introduced followed by H2 (14 atm). The reaction vessel was cooled to -60° C. and CO2 (78 atm) was introduced. The mixture was allowed to stir at 65° C. and 100 atm overnight. The autoclave was cooled to 0° C. and all the gasses were carefully released. The GC analysis showed that the conversion of the reaction was 91% and the ratio of 3-phenylpropanal to (R)-2-phenylpropanal was 1:12.5. The enantiomeric purity of 2-phenylpropanal thus formed was determined to be 85% enantiomeric excess by converting it to (R)-2-phenylpropanol followed by esterification with (S)-methoxy(trifluoromethyl)phenylacetyl chloride in the presence of triethylamine in CH2Cl2, and subjecting the resulting chiral ester to the 1H NMR analysis.
Workup
- additionwas introduced
- custom100 atm overnight
- temperatureThe autoclave was cooled to 0° C.
Sources & evidence
- ORD record
- ord-5e7cf5694d77439a999cd4c86534974c
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05962744
Reaction notes
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