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

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.

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)

ORD record

ord-47be3158f6f24b5fa2aaa0a65fe0104b

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088791B2