67809-85-2 → 1-(3,3,5,5-Tetramethyl-cyclohexyl)-ethanol

HRID 1045057Notes

Reaction equation

HRID 1045057 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([CH:10]=[O:11])[CH2:3]1.[CH3:13][Mg]Br>C1COCC1>[CH3:9][C:6]1([CH3:8])[CH2:7][C:2]([CH3:12])([CH3:1])[CH2:3][CH:4]([CH:10]([OH:11])[CH3:13])[CH2:5]1

Participants

4

Reactant 2

HCID 2168772067809-85-2HCID 178418573HCID 178418573, compound

Product 1

HCID 671807551-(3,3,5,5-Tetramethyl-cyclohexyl)-ethanolYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude 3,3,5,5-Tetramethyl-cyclohexanecarboxaldehyde (650 mg, 3.8 mmol) was treated with methylmagnesium bromide (4.5 mmol, 1.2 eq) in THF (20 mL) at 0° C., and allowing to warm to RT following a method analogous to General Procedure I to produce 1-(3,3,5,5-tetramethyl-cyclohexyl)-ethanol (400 mg) after quenching the reaction at 0° C. with 2N HCl, extraction of the product with EtOAc, and evaporation of the solvent under vacuum. The crude material was used without purification in the next step.

Sources & evidence

ORD record
ord-1182a10caa254223ae0e7a7b7d933f40
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Reaction notes

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