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

HRID 323929Notes

Reaction equation

HRID 323929 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.Cl.[CH3:13]O>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 313Hydrochloric AcidHCID 887Methanol

Product 1

HCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterYield 95.1%

Procedure

To 200 mL of methanol, was added 6.3 g of p-hydroxyphenylacetic acid. Ten droplets of concentrated hydrochloric acid was added to the resulting mixture by a Pasteur pipet and reaction proceeded at 80° C. for 1 hour. The mixture was concentrated, mixed with 100 mL of ethyl acetate, and washed twice with 50 mL of distilled water. The resultant was dried over sodium sulfate, filtered, concentrated, and dried under reduced pressure. As a result, 6.5 g (95.1%) of methyl p-hydroxyphenylacetate was obtained.

Workup

  1. concentrationThe mixture was concentrated
  2. additionmixed with 100 mL of ethyl acetate
  3. washwashed twice with 50 mL of distilled water
  4. dry with materialThe resultant was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-926ec8e1411b431da451350c295d8b3e
Source dataset
uspto-grants-2001_04
Patent number
US06215016B1

Reaction notes

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