Acetic Anhydride → 3-Chloro-4-acetoxybenzoic acid

HRID 224476

Reaction equation

HRID 224476 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[C:12](OC(=O)C)(=[O:14])[CH3:13]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12](=[O:14])[CH3:13])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 198603-Chloro-4-hydroxybenzoic acid

Product 1

HCID 106562963-Chloro-4-acetoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
135 °C

Procedure

A solution was prepared from 100 g of the commercially available hemihydrate of 3-chloro-4-hydroxybenzoic acid in 300 mL of acetic anhydride. After adding 7 drops of concentrated sulfuric acid, the mixture was refluxed at 135° C. for 2 hrs. The product crystallized out on cooling. About 500 mL of cold water was added with stirring, which continued while cooling in an ice/water bath for 1 hr. After filtration and drying, the product was recrystallized from 350 mL of ethyl alcohol to yield 40 g of 3-chloro-4-acetoxybenzoic acid melting at 152-159° C.

Workup

  1. customThe product crystallized out
  2. temperatureon cooling
  3. additionAbout 500 mL of cold water was added
  4. temperaturewhile cooling in an ice/water bath for 1 hr
  5. filtrationAfter filtration
  6. customdrying
  7. customthe product was recrystallized from 350 mL of ethyl alcohol

Sources & evidence

ORD record
ord-09439c07602948ff8de07be943ecec60
Source dataset
uspto-grants-1980_11
Patent number
US04232144

Linked notes

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