Hydrochloric Acid → Methyl 2-(4-hydroxyphenoxy)acetate

HRID 1707997Notes

Reaction equation

HRID 1707997 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.Cl.[CH3:14]O>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([O:10][CH3:14])=[O:9])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 15881(4-Hydroxyphenoxy)acetic acid

Product 1

HCID 602731Methyl 2-(4-hydroxyphenoxy)acetate

Procedure

A solution of 4-hydroxyphenoxyacetic acid (33.6 g) in methanol was treated with hydrogen chloride gas and left to stand at ambient temperature overnight. The solvent was removed in vacuo and the residue taken up in ethyl acetate. This solution was washed sequentially with saturated sodium hydrogen carbonate solution (2×100 ml) and brine (100 ml), then dried (MgSO4) and the solvent evaporated to give methyl 4-hydroxyphenoxyacetate as a colourless crystalline mass, m.p. 112°-114° C.; NMR: 3.8 (s, 3H, CH3), 4.55 (s, 2H, CH2), 6.75 (s, 4H, phenyl-H) 6.8-7.8 (broad s, 1H, OH); m/e 200 (M+NH4)+.

Workup

  1. waitleft
  2. customThe solvent was removed in vacuo
  3. washThis solution was washed sequentially with saturated sodium hydrogen carbonate solution (2×100 ml) and brine (100 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-1b8ef5ddcb2e45f4a7e879669a8824ed
Source dataset
uspto-grants-1994_10
Patent number
US05356894

Reaction notes

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