Sodium borohydride → (4-(Benzyloxy)-2,6-dimethylphenyl)methanol

HRID 1013806Notes

Reaction equation

HRID 1013806 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([CH3:17])[C:12]([CH:13]=[O:14])=[C:11]([CH3:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH3:18])[C:12]([CH2:13][OH:14])=[C:15]([CH3:17])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 111608034-(Benzyloxy)-2,6-dimethylbenzaldehyde

Product 1

HCID 67317571(4-(Benzyloxy)-2,6-dimethylphenyl)methanolYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Treat a solution of 4-Benzyloxy-2,6-dimethyl-benzaldehyde (6.4 g, 27 mmol) in Methanol (60 mL) with Sodium borohydride (0.82 g, 22 mmol). Stir the reaction for 1 hr at room temperature. Quench the reaction with a saturated solution of sodium bicarbonate in water and extract with Et2O. Wash the organic with brine, dry over MgSO4, and filter. Remove the solvent to afford 6.3 g (97%) of product. 1H NMR (d6-CDCl3) δ 7.31-7.43 (m, 5H), 6.65 (s, 2H), 5.01 (s, 2H), 4.66 (s, 2H), 2.38 (s, 6H).

Workup

  1. customthe reaction for 1 hr at room temperature
  2. customQuench
  3. customthe reaction with a saturated solution of sodium bicarbonate in water
  4. extractionextract with Et2O
  5. washWash the organic with brine
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customRemove the solvent

Sources & evidence

ORD record
ord-c8738ca60e3e43f6bde34b7a427ade02
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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