Sulfuric Acid → 3,4-Dichlorophenyl acetate

HRID 1722038Notes

Reaction equation

HRID 1722038 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:10](OC(=O)C)(=[O:12])[CH3:11].S(=O)(=O)(O)O>O>[C:10]([O:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 72583,4-DichlorophenolHCID 7918Acetic Anhydride

Product 1

HCID 5194813,4-Dichlorophenyl acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature, 3,4-dichlorophenol (298.5 g, 1.83 mol) was dissolved in 191 ml (207 g, 2.02 mol) of acetic anhydride in a 1 liter flask equipped with mechanical stirrer and condenser. Sulfuric acid (3 ml) was added, resulting in a strong exotherm. After 2 hours the mixture was poured into 2 liters of ice and water and extracted 3×1 liter diethyl ether. The organic layers were combined, washed 1×1 liter water, 2×1 liter saturated sodium bicarbonate and 1×1 liter saturated brine, dried over magnesium sulfate and stripped to yield title product as an orange oil, 375 g, tlc Rf 0.5 (1:1 diethyl ether:hexane).

Workup

  1. customequipped with mechanical stirrer and condenser
  2. customresulting in a strong exotherm
  3. extractionextracted 3×1 liter diethyl ether
  4. washwashed 1×1 liter water, 2×1 liter saturated sodium bicarbonate and 1×1 liter saturated brine
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-9589874d637c4fcfa04c2afc6f9c1229
Source dataset
uspto-grants-1989_08
Patent number
US04853410

Reaction notes

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