Chloroacetyl chloride → Ethyl Acetate

HRID 59638Notes

Reaction equation

HRID 59638 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]([CH:12]=[CH:13][C:7]=2[CH:6]=[CH:5][C:4]=1[OH:14])=[O:11].[Cl:15][CH2:16][C:17](Cl)=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Cl:15][CH2:16][C:17]([O:14][C:4]1[C:3]([O:2][CH3:1])=[C:8]2[C:7]([CH:13]=[CH:12][C:10](=[O:11])[O:9]2)=[CH:6][CH:5]=1)=[O:18].[C:10]([O:9][CH2:8][CH3:7])(=[O:11])[CH3:12]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 53163027-Hydroxy-8-methoxycoumarin

Product 2

HCID 8857Ethyl AcetateYield 90%HCID 118376976HCID 118376976, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.8 g of hydrangetin (0.01 mole) is acetylated with 1.35 g of 2-chloroacetyl chloride (0.012 mole) by heating at 80° C. in dimethylformamide in the presence of sodium carbonate. After vacuum filtration and evaporation, 7-(2′-chloroacetyloxy)-8-methoxycoumarin (compound A) is isolated by crystallization in ethyl acetate (yield 90%).

Workup

  1. filtrationAfter vacuum filtration and evaporation

Sources & evidence

ORD record
ord-0dc208a260cf4cd0b83ae056c3399b7e
Source dataset
uspto-grants-2016_09
Patent number
US09440940B2

Reaction notes

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