Cyclohexanebutanoic acid → Cyclohexanebutanol

HRID 2287102Notes

Reaction equation

HRID 2287102 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C:10](O)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 75200Cyclohexanebutanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 78182Cyclohexanebutanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-cyclohexylbutyric acid (Aldrich) is reduced with excess lithium aluminum hydride in ether to yield 4-cyclohexyl-1-butanol (D. S. Hiers and R. Adams, J. Am. Chem. Soc., 45 2385 (1926)) which is chloro-methylated with hydrogen chloride and formaldehyde to yield the desired compound.

Sources & evidence

ORD record
ord-65b5d2c97cfa46eca17e8feab45c87a4
Source dataset
uspto-grants-1981_05
Patent number
US04268692

Reaction notes

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