Sodium borohydride → 5-(tert-Butyl)-2-(hydroxymethyl)phenol

HRID 2377428Notes

Reaction equation

HRID 2377428 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:19]=[O:20])=[C:9]([O:11]S(C(F)(F)F)(=O)=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(C=O)=C(O)C=1)(C)(C)C.[BH4-].[Na+]>CO.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:19][OH:20])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 137652724-tert-Butyl-2-hydroxybenzaldehydeHCID 57424249Trifluoro-methanesulfonic acid 5-tert-butyl-2-formyl-phenyl ester2×

Product 1

HCID 196902415-(tert-Butyl)-2-(hydroxymethyl)phenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A stirred, cooled (ice-bath) solution of a 1:1 mixture of trifluoro-methanesulfonic acid 5-tert-butyl-2-formyl-phenyl ester and 4-tert-butyl-2-hydroxy-benzaldehyde (Intermediate 105, 0.47 g) in methanol (8 mL) was treated with sodium borohydride (0.1 g, 2.64 mmol). After 1 h, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue that was subjected to flash column chromatography on silica gel (230-400 mesh) to afford the title product (0.3 g).

Workup

  1. temperatureA stirred, cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to a residue that

Sources & evidence

ORD record
ord-39664e0de7e54f7693bca9de710658cc
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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