Hydroxyphenylacetic acid → Benzeneacetic acid, 4-hydroxy-, methyl ester

HRID 374835Notes

Reaction equation

HRID 374835 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12]O.O=S(Cl)Cl>C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 887MethanolHCID 24386Thionyl Chloride

Product 1

HCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-hydroxyphenylacetic acid (9.12 g, 0.06 mol), methanol (50 mL) and SOCl2 (2 mL, 0.028 mol) was refluxed for 3 hours. The residue was cooled, diluted with ethyl acetate (20 mL), washed-first with aqueous 5% Na2CO3 solution and then twice with water (100 mL), then dried over anhydrous MgSO4, filtered and evaporated in vacuo to give methyl 4-hydroxyphenylacetate as an oil.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureThe residue was cooled
  3. washwashed-first with aqueous 5% Na2CO3 solution
  4. dry with materialtwice with water (100 mL), then dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-aa0a13d83d734163931ac6f131b80adf
Source dataset
uspto-grants-1996_01
Patent number
US05482961

Reaction notes

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