4-Hydroxybenzoic Acid → 4-[(Methoxycarbonyl)oxy]benzoic acid

HRID 343259Notes

Reaction equation

HRID 343259 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[CH3:13][O:14][C:15](Cl)=[O:16].Cl.O>O>[CH3:13][O:14][C:15]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)=[O:16]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 21885828Hydrate;hydrochloride

Product 1

HCID 222422684-[(Methoxycarbonyl)oxy]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (15 g) in water (400 ml) was chilled to 0° C. in ice. To this the 4-hydroxy benzoic acid (17.9 g, 0.130 mol) was added. Methylchloroformate (20 g, 0.212 mol) was added slowly to prevent the temperature from rising above 5° C. The reaction mixture was stirred at 0°-5° C. for 3 h during which time a white suspension gradually formed. The pH was adjusted to 4-5 with addition of HCl/water (1:1). The voluminous precipitate was filtered off, washed with water and recrystallised from ethanol (200 ml).

Workup

  1. customfrom rising above 5° C
  2. customgradually formed
  3. filtrationThe voluminous precipitate was filtered off
  4. washwashed with water
  5. customrecrystallised from ethanol (200 ml)

Sources & evidence

ORD record
ord-a6639ac7d8e049699da50826cc9d1988
Source dataset
uspto-grants-1999_01
Patent number
US05861109

Reaction notes

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