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

HRID 546362Notes

Reaction equation

HRID 546362 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-f7824de263db4cf6a63921c5fb3d5eb4
Source dataset
uspto-grants-2011_05
Patent number
US07935843B2

Reaction notes

Loading…