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

HRID 326950Notes

Reaction equation

HRID 326950 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 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an aqueous solution of 55 mmol (7.6 g) of p-hydroxybenzoic acid and 65 mmol (2.6 g) of sodium hydroxide in 200 ml of water was added 65 mmol (10.6 g) of carbobenzoxy chloride dropwise during cooling with ice. After 24 hours, the generated precipitate was washed with water, filtered, dried, and purified by column chromatography, to obtain 15.0 g of 4-carbobenzoxyoxybenzoic acid (m.p.: 181.9°-183.1° C.). (Yield: 99%)

Workup

  1. temperatureduring cooling with ice
  2. washthe generated precipitate was washed with water
  3. filtrationfiltered
  4. customdried
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-453e6102ffc744dcbd13248bd7842b9c
Source dataset
uspto-grants-1993_12
Patent number
US05271866

Reaction notes

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