Acetic Acid → Benzoic acid, 4-hydroxy-, carboxymethyl ester

HRID 2065437Notes

Reaction equation

HRID 2065437 reaction equation
C([O:5][C:6]([CH2:8][O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:7])(C)(C)C.[OH-].[Li+].C(O)(=O)C>O1CCCC1>[C:6]([CH2:8][O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 584275094-Hydroxy-benzoic acid tert-butoxycarbonylmethyl ester

Product 1

HCID 58427513Benzoic acid, 4-hydroxy-, carboxymethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4-hydroxy-benzoic acid tert-butoxycarbonylmethyl ester 15 (18 grams, 71.42 mmol) in tetrahydrofuran (100 mL) is added 10% lithium hydroxide solution (35 mL). The mixture is heated at 50-60° C. for 1 hour. The reaction mass is cooled to room temperature, and the pH is adjusted to 4 with dilute acetic acid. The organic phase is separated and distilled to give crude 16, which can be purified in appropriate solvent.

Workup

  1. temperatureThe reaction mass is cooled to room temperature
  2. customThe organic phase is separated
  3. distillationdistilled
  4. customto give crude 16, which
  5. customcan be purified in appropriate solvent

Sources & evidence

ORD record
ord-16d564569f1d4bb6b4b547a8601f331f
Source dataset
uspto-grants-2012_10
Patent number
US08288505B2

Reaction notes

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