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

HRID 1580181Notes

Reaction equation

HRID 1580181 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 was 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.

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-4a7b3dab7b294a9e8819ad766e7c2d5f
Source dataset
uspto-grants-1976_01
Patent number
US03932466

Reaction notes

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