Benzaldehyde → (R)-(+)-1-Phenyl-1-propanol

HRID 376479Notes

Reaction equation

HRID 376479 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([Zn]CC)[CH3:10]>>[C:2]1([C@H:1]([OH:8])[CH2:9][CH3:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 178418750HCID 178418750, compound

Product 1

HCID 640199(R)-(+)-1-Phenyl-1-propanolYield 90%

Procedure

Reaction of benzaldehyde with diethylzinc in the presence of the polymer of Example 6 to give (R)-1-phenyl-1-propanol. The polymer of Example 6 (Mw=24,300 and Mn=9900, PDI=2.45) was used to catalyze the addition reaction of diethylzinc to an aldehyde according to the procedure of Example 4. For benzaldehyde, the yield was 90% with ee of 92.7% ((R) product). For p-chloro-benzaldehyde, the yield was 95% with ee of 93.8% ((R) product).

Sources & evidence

ORD record
ord-46f143c8eccc42b59de5db937881ea9d
Source dataset
uspto-grants-2000_02
Patent number
US06020452

Reaction notes

Loading…