Methanol → Methyl 3-Hydroxyphenylacetate

HRID 744124Notes

Reaction equation

HRID 744124 reaction equation
S(=O)(=O)(O)O.[OH:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=1.[CH3:17]O>>[OH:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 39129Methyl 3-HydroxyphenylacetateYield 98%

Procedure

A catalytic quantity of concentrated sulphuric acid (1.0 ml) was added to a solution of (3-hydroxy)phenylacetic acid (17.38 g, 0.114 mol) in methanol (100 ml). The reaction mixture was stirred for 3 hours at room temperature and then concentrated in vacuo. The residue was partitioned between diethyl ether (200 ml) and a saturated aqueous solution of sodium hydrogen carbonate (200 ml). The ether phase was separated and washed with non-saturated sodium hydrogen carbonate solution (200 ml) and saturated brine solution (100 ml). The ether extract was dried over magnesium sulphate. The solvent was evaporated and the residue dried to afford methyl 3-hydroxyphenylacetate as an amber oil (18.61 g, 98%); δH (360 MHz, CDCl3) 3.58 (2H, s, CH2), 3.70 (3H, s, COOCH3), 5.54 (1H, br s, OH), 6.74 (2H, m, ArH), 6.81 (1H, d, J 8 Hz, ArH), 7.17 (1H, t, J 8 Hz, ArH).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between diethyl ether (200 ml)
  3. customThe ether phase was separated
  4. washwashed with non-saturated sodium hydrogen carbonate solution (200 ml) and saturated brine solution (100 ml)
  5. extractionThe ether extract
  6. dry with materialwas dried over magnesium sulphate
  7. customThe solvent was evaporated
  8. customthe residue dried

Sources & evidence

ORD record
ord-41af97eff827474eb3b4db47187d833d
Source dataset
uspto-grants-1996_09
Patent number
US05559125

Reaction notes

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