Acetic Anhydride → 3-CHLOROPHENYL ACETATE

HRID 1786519Notes

Reaction equation

HRID 1786519 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].[Na]>S(=O)(=O)(O)O>[C:9]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 79333-ChlorophenolHCID 5360545Sodium

Product 1

HCID 830613-CHLOROPHENYL ACETATE

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
120 °C

Procedure

3-Chlorophenol (100 g, 0.78 mol) was dissolved in acetic anhydride (75 mL, 0.8 mol). Upon addition of 1 drop of concentrated sulfuric acid, the temperature raised to 120° C. After 45 minutes, the mixture was cooled and poured into a solution of sodium hydrogenocarbonate (8 g in 1 L of water) and extracted with diethylether. The organic layer was washed with a saturated sodium hydrogenocarbonate solution, dried over magnesium sulfate and evaporated under reduced pressure. The resulting oil was used directly in the next step (84%). IR (KBr): υ: 3072 (C—H aromatic), 2939 (C—H aliphatic), 1773 (C═O), 1196 (C—O) cm−1.

Workup

  1. temperaturethe mixture was cooled
  2. extractionextracted with diethylether
  3. washThe organic layer was washed with a saturated sodium hydrogenocarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-25375e3403b849d89b8e5f17ac754ba2
Source dataset
uspto-grants-2009_03
Patent number
US07507761B2

Reaction notes

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