Acetic Anhydride → 2-(Acetyloxy)-5-chlorobenzoic acid

HRID 2398091Notes

Reaction equation

HRID 2398091 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>S(=O)(=O)(O)O>[C:12]([O:11][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 94475-Chlorosalicylic Acid

Product 1

HCID 28208132-(Acetyloxy)-5-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
40 °C

Procedure

A mixture of 86 g (0.5 mole) of 5-chloro salicylic acid and 102 g (1.0 mole) of acetic anhydride are warmed to 40° C. With stirring, 5 drops of conc. sulfuric acid are added, which causes an exothermic reaction. The mixture is stirred for 1/2 hour at 60° C. then poured into ice. The solid is filtered, washed with water and air dried, mp 146°-8° C, and is used as is for the next step. ##STR5##

Workup

  1. customan exothermic reaction
  2. stirringThe mixture is stirred for 1/2 hour at 60° C.
  3. additionthen poured into ice
  4. filtrationThe solid is filtered
  5. washwashed with water and air
  6. customdried

Sources & evidence

ORD record
ord-a18ce45e8e844033b15a42552093486d
Source dataset
uspto-grants-1977_05
Patent number
US04024160

Reaction notes

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