Acetic Anhydride → HCID 20489647, compound

HRID 1995069Notes

Reaction equation

HRID 1995069 reaction equation
[C:1]([C:4]1[C:14]([Cl:15])=[CH:13][C:12]([Cl:16])=[CH:11][C:5]=1[O:6][CH2:7]C(O)=O)(=O)[CH3:2].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>C(=O)(O)[O-].[Na+]>[Cl:15][C:14]1[C:4]2[C:1]([CH3:2])=[CH:7][O:6][C:5]=2[CH:11]=[C:12]([Cl:16])[CH:13]=1

Participants

5

Reactant 3

HCID 7918Acetic Anhydride2×HCID 517045Sodium AcetateHCID 54573285HCID 54573285, compound

Product 1

HCID 20489647HCID 20489647, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 5.0 g (0.019 mol) of 2-(2-acetyl-3,5-dichlorophenoxy) acetic acid, 10.0 g of anhydrous sodium acetate and 50 ml of acetic anhydride was heated at 155° C. for 0.5 hour. The mixture was poured on to 100 g of ice and 100 ml of a saturated sodium bicarbonate solution. When decomposition of the excess acetic anhydride was complete, the mixture was extracted with three 100 ml portions of diethyl ether. The combined extracts were washed neutral with saturated sodium bicarbonate solution, dried over sodium sulphate and evaporated to give a brown oil which solidified on standing. The crude product was purified by distillation to yield 2.4 g of pure 4,6-dichloro-3-methylbenzofuran of boiling point 85° C./1 mmHg. The distilled product could be crystallized from petrol (boiling point 40°-60° C.) in the form of white needles of melting point 45° C.

Workup

  1. extractionthe mixture was extracted with three 100 ml portions of diethyl ether
  2. washThe combined extracts were washed neutral with saturated sodium bicarbonate solution
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customto give a brown oil which
  6. distillationThe crude product was purified by distillation

Sources & evidence

ORD record
ord-e00f00d5ac324e87b725962a4d4bf00a
Source dataset
uspto-grants-1983_09
Patent number
US04402968

Reaction notes

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