Water → 5-Benzyloxy-2-hydroxymethylphenol

HRID 1891434Notes

Reaction equation

HRID 1891434 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].OS(O)(=O)=O.O>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:17])[C:12](=[CH:15][CH:16]=1)[CH2:13][OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 5612354-Benzyloxy-2-hydroxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 251384215-Benzyloxy-2-hydroxymethylphenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the benzaldehyde G3a (127.5 g, 0.52 mol) in MeOH (1 L) at 0 ° C., NaBH4 (16 g, 0.42 mol) was added. The reaction mixture was stirred for 18 h at rt. Reaction progress was monitored by TLC. Upon completion, the reaction mixture was reduced to one-fourth volume and was treated with 0.5 N aq H2SO4 to adjust pH to about 6-7 followed by addition of H2O (1 L). Upon vigorous stirring white precipitate formed. After filtration, the precipitate was lyophilized, washed using chilled toluene (ca. −50° C.) and dried under vacuum to obtain G3 (89 g, 0.38 mol, 73%) as an off-white solid: mp 86-88° C. (Lit.8 88-90° C.); 1H NMR (DMSO, 400 MHz) δ 9.33 (1H, s), 7.35 (5H, m,) 7.08 (1H, d, J=8.4 Hz), 6.42 (2H, m), 5.01 (2H, s), 4.80 (1H, m), 4.39 (2H, s).

Workup

  1. customReaction progress
  2. customUpon vigorous stirring white precipitate formed
  3. filtrationAfter filtration
  4. washwashed
  5. temperatureusing chilled toluene (ca. −50° C.)
  6. customdried under vacuum
  7. customto obtain G3 (89 g, 0.38 mol, 73%) as an off-white solid
  8. custommp 86-88° C. (Lit.8 88-90° C.)

Sources & evidence

ORD record
ord-e69504a090da4ed3b7d6b78fc534fca2
Source dataset
uspto-grants-2013_08
Patent number
US08507549B2

Reaction notes

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