Citronellal → Cyclohexanol, 5-methyl-2-(1-methylethenyl)-

HRID 1835973Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][C@@H:6]([OH:8])[C@H:5]([C:9]([CH3:11])=[CH2:10])[CH2:4][CH2:3]1.CC(=CCCC(CC=O)C)C>>[CH3:1][CH:2]1[CH2:7][CH:6]([OH:8])[CH:5]([C:9]([CH3:11])=[CH2:10])[CH2:4][CH2:3]1

Participants

Reactant 2

HCID 7794Citronellal

HCID 170833(-)-Isopulegol

Product 1

HCID 24585Cyclohexanol, 5-methyl-2-(1-methylethenyl)-Yield 95.1%

Procedure

In Example 15, isopulegol was synthesized in the same manner as in Example 1, except for replacing d-citronellal with 5.00 g of dl-citronellal. As a result, dl-isopulegol was obtained in a yield of 95.1%, and the ratio of dl-isopulegol to other isomers was 99.4/0.6.

Sources & evidence

ORD record: ord-5e4fcff0a5d64276b691bfcc184f4e6c
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06774269B2

Reaction notes

Loading…