Hydrochloric Acid → 4-(Carboxymethoxy)benzoic acid

HRID 2405188Notes

Reaction equation

HRID 2405188 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]([O:14]C)=[O:13])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>O>[C:12]([CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:16])=[O:2])=[CH:5][CH:6]=1)([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 887006methyl 4-(2-methoxy-2-oxoethoxy)benzoate

Product 1

HCID 880244-(Carboxymethoxy)benzoic acidYield 91.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4-Methoxycarbonylmethoxy-benzoic acid methyl ester 1 (50 grams, 223 mmol) was added to a solution of 2.5 M sodium hydroxide (250 mL) and heated to 80° C. for 5 hours. The reaction mixture was dilated with water (100 mL) and pH adjusted to 1 with concentrated HCl. Crude 76 was filtered, dried and given hot ethyl acetate slurry to give 76 (40 grams, 91.4%) as a white powder. M.p: >280° C.

Workup

  1. filtrationCrude 76 was filtered
  2. customdried

Sources & evidence

ORD record
ord-cc01f91bedae4e3daac2497c047e641f
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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