3,5-Bis(tert-butyl)benzoic acid → (3,5-Di-tert-butylphenyl)methanol

HRID 964926Notes

Reaction equation

HRID 964926 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:13]=1)[C:8](O)=[O:9])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:14]([C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:13]=1)[CH2:8][OH:9])([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 1

HCID 853393,5-Bis(tert-butyl)benzoic acid

Product 1

HCID 12660843(3,5-Di-tert-butylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1 g of 3,5-di-t-butylbenzoic acid dissolved in THF (10 mL) was added at 25° C. a solution of 1M BH3 ·THF (4 mL), and the mixture was stirred at this temperature for 1.5 hours. The mixture was quenched with 1N NaOH (4 mL) and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and evaporated to give 3, 5-di-t-butylbenzyl alcohol as a clear oil which was used directly in the next step.

Workup

  1. customThe mixture was quenched with 1N NaOH (4 mL)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-a2aefeab37af4eaa988a21e65994e08e
Source dataset
uspto-grants-1998_06
Patent number
US05773421

Reaction notes

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