Chloroacetyl chloride → HCID 86682017, compound

HRID 1749860Notes

Reaction equation

HRID 1749860 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH2:6][C:7](Cl)=[O:8].[CH3:10][C:11]([C:13]1[C:14]([OH:20])=[CH:15][CH:16]=[CH:17][C:18]=1[OH:19])=[O:12].C(OCC)(=O)C>[N+](C1C=CC=CC=1)([O-])=O>[C:11]([C:13]1[C:14]2[O:20][CH2:6][C:7](=[O:8])[C:15]=2[CH:16]=[CH:17][C:18]=1[OH:19])(=[O:12])[CH3:10]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8857Ethyl AcetateHCID 696872',6'-DihydroxyacetophenoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 86682017HCID 86682017, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Conditions

Temperature
0 °C

Procedure

The synthesis was performed with reference to the known literature (Journal of the Pharmaceutical Society of Japan (Yakugaku Zasshi), Vol. 88, p. 589, 1968). A suspension of aluminum chloride (3.5 g, 26 mmol) in nitrobenzene (10 mL) was stirred at 0° C. under an argon atmosphere. This suspension was added with chloroacetyl chloride (1.1 g, 9.9 mmol), and then the mixture was added dropwise with a suspension of 2,6-dihydroxyacetophenone (1.0 g, 6.6 mmol) in nitrobenzene (6.0 mL). After completion of the addition, the reaction mixture was stirred at 50° C. for 17 hours. The reaction mixture was added with ethyl acetate and ice water, the mixture was stirred at room temperature for 1 hour, and then the organic layer was separated. The organic layer was extracted with 1 N aqueous sodium hydroxide, and the aqueous layer was made acidic with 3 N hydrochloric acid to precipitate solid. The precipitated solid was collected by filtration and dried to obtain 7-acetyl-6-hydroxybenzofuran-3(2H)-one (0.90 g, 71%).

Workup

  1. additionAfter completion of the addition
  2. stirringthe reaction mixture was stirred at 50° C. for 17 hours
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. customthe organic layer was separated
  5. extractionThe organic layer was extracted with 1 N aqueous sodium hydroxide
  6. customto precipitate solid
  7. filtrationThe precipitated solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-608ae42f17a0417383d57ea7d7f51a79
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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