Methanol → Methyl 3-Hydroxyphenylacetate

HRID 2108714Notes

Reaction equation

HRID 2108714 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[CH3:17]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:17])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 39129Methyl 3-Hydroxyphenylacetate

Procedure

3-Hydroxyphenylacetic acid (75.3 g, 0.5 mol) was dissolved in methanol (900 mL). Concentrated sulfuric acid (2 mL) was added and the mixture refluxed for 5 hours. The solvent was evaporated and the residue dissolved in ethyl acetate (1000 mL) and washed with water (2×600 mL) and brine, and dried (MgSO4). Solvent was evaporated to afford methyl 3-hydroxyphenylacetate as an oil (82 g, quantitative yield). 1H NMR (500 MHz, CDCl3) δ 7.2 (1H, t), 6.9-6.75 (3H, m), 5.5 (1H, br), 3.75 (3H, s), 3.63 (2H, s).

Workup

  1. temperaturethe mixture refluxed for 5 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate (1000 mL)
  4. washwashed with water (2×600 mL) and brine
  5. dry with materialdried (MgSO4)
  6. customSolvent was evaporated

Sources & evidence

ORD record
ord-b7b3b1b4d25a475eb66e8748c1747334
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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