3-Hydroxybenzyl alcohol → 3-(Hydroxymethyl)phenyl acetate

HRID 538529Notes

Reaction equation

HRID 538529 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[OH-].[K+].[C:12](OC(=O)C)(=[O:14])[CH3:13]>O>[C:12]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH2:5][OH:6])[CH:3]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 7918Acetic AnhydrideHCID 14797Potassium Hydroxide

Product 1

HCID 139456123-(Hydroxymethyl)phenyl acetateYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 3-hydroxybenzylalcohol (1.0 g, 8 mmol, 1 equiv.) in 6.4N KOH solution (1.86 ml, 12 mmol, 1.5 equiv.) at r.t., ice (4 g) was added followed by acetic anhydride (0.95 ml, 10 mmol, 1.25 equiv.). The reaction mixture was stirred at r.t. for 3 h. Water (50 ml) was added and the mixture was stirred for 30 min, before extracting with CH2Cl2 (2×50 ml). The combined organic extracts were washed with brine (50 ml), dried (Na2SO4) and evaporated to dryness, under reduced pressure. The clear oil residue was purified by column chromatography on silica, eluted with EtOAc/hexane (1:2), to give the desired product as a clear oil (714 mg, 54% yield). HPLC-MS (method 1): m/z 165 [M−H]−. Rt=2.52 min.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. extractionbefore extracting with CH2Cl2 (2×50 ml)
  3. washThe combined organic extracts were washed with brine (50 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness, under reduced pressure
  6. customThe clear oil residue was purified by column chromatography on silica
  7. washeluted with EtOAc/hexane (1:2)

Sources & evidence

ORD record
ord-787d66037d684c92951e13a909cb68c9
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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