4-Hydroxybenzoic Acid → 4-{[(Benzyloxy)carbonyl]oxy}benzoic acid

HRID 2082184Notes

Reaction equation

HRID 2082184 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[C:13](Cl)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>O>[C:13]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 179141024-{[(Benzyloxy)carbonyl]oxy}benzoic acidYield 100.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an aqueous solution of 55 m moles (7.6 g) of 4-hydroxybenzoic acid and 65 m moles (2.6 g) of sodium hydroxide in 200 ml of water, 65 m moles (10.6 g) of carbobenzoxychloride was added dropwise at 0° C. After 24 hours, the precipitate was washed with water, filtered, and dried, then purified by column chromatography to obtain 15.0 g of 4-carbobenzoxyoxybenzoic acid [m.p. 181.9°-183.1° C⟧ (yield:99%)

Workup

  1. washthe precipitate was washed with water
  2. filtrationfiltered
  3. customdried
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-6db95bc763d941a3ac571da85047bed2
Source dataset
uspto-grants-1993_02
Patent number
US05187298

Reaction notes

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