3-Methylcyclohexanecarboxylic acid → (3-Methylcyclohexyl)methanol

HRID 1533885Notes

Reaction equation

HRID 1533885 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8](O)=[O:9])[CH2:3]1>O1CCCC1.CCOCC>[OH:9][CH2:8][CH:4]1[CH2:5][CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3]1

Participants

4

Reactant 1

HCID 1144903-Methylcyclohexanecarboxylic acid

Product 1

HCID 15004795(3-Methylcyclohexyl)methanolYield 74.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a boran-methyl sulfide complex (1.7 ml, 0.028 mole) in 7 ml tetrahydrofuran, at 0° C., was added dropwise 2 g of 3-methylcyclohexanecarboxylic acid (0.014 mole) in 7 ml tetrahydrofuran. Stirring was continued for one hour. The reaction mixture was diluted with ether and washed with 1N aqueous sodium hydroxide and then with brine. Concentration and distillation gave 1.34 g of the title compound The NMR spectrum showed absorption at 0.54-0.74 (m, 1H), 0.90, 0.93 (s, 3H), 1.17-1.53 (m, 3H), 1.65-1.77 (m, 3H) and 3.39-3.52 (m, 2H).

Workup

  1. washwashed with 1N aqueous sodium hydroxide
  2. concentrationConcentration and distillation

Sources & evidence

ORD record
ord-9741e3c8d59d414fb45fe17c1d5dc5aa
Source dataset
uspto-grants-1992_02
Patent number
US05086062

Reaction notes

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