1-Phenylethanol → Acetophenone
Reaction equation
C1([C@@H](NCCN[C@H](C2C=CC=CC=2)C)C)C=CC=CC=1.[CH3:21][CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[OH:23]>C([Zn]CC)C>[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])[CH3:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
The procedure was the same as in Example 11, using diethylzinc (1 mmol) as catalyst and N,N′-bis-(1-(S)-phenylethyl)-1,2-ethylenediamine in a quantity five times less, i.e. 0.2 mmol, as ligand. After the mixture had been stirred at 20° C. for 24 hours, hydrolysis was carried out with a 30% excess of soda, and a mixture of methylphenylcarbinol comprising 88% of the (S) isomer and 12% of the (R) isomer, that is to say, an ee of 74%, was recovered with a yield of 95%.
Workup
- customhydrolysis
- customan ee of 74%, was recovered with a yield of 95%
Sources & evidence
- ORD record
- ord-9e454689c34b4a90aabfc516a8bcbaec
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06573395B2
Reaction notes
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