4-Tert-butylcyclohexane-1-carboxylic acid → 4-tert-Butylcyclohexylmethanol

HRID 892162

Reaction equation

HRID 892162 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11](O)=[O:12])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([CH2:11][OH:12])[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 1367594-Tert-butylcyclohexane-1-carboxylic acid

Product 1

HCID 827594-tert-Butylcyclohexylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (0° C.) solution of 4-tert-butylcyclohexane-carboxylic acid (3.00 g, 16.3 mmoles) in THF (30 mL) is slowly added a THF solution of borane-THF complex (1.0M, 21.2 mL, 21.2 mmoles). The solution is stirred at room temperature for 18 hours, then quenched with 2N HCl solution (30 mL), and extracted with EtOAc. The organic layer is isolated, washed with 1N NaOH, dried over sodium sulfate, and concentrated to yield the title compound as a clear oil. 1H NMR (300 MHz, CDCl3): δ 2.06 (d, 2H), 1.82 (m, 4H), 1.52 (m, 2H), 0.88 (m, 4H), 0.83 (s, 9H).

Workup

  1. customquenched with 2N HCl solution (30 mL)
  2. extractionextracted with EtOAc
  3. customThe organic layer is isolated
  4. washwashed with 1N NaOH
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a6bf99dfdd46429099e8362ac7e4f668
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Linked notes

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