Potassium Carbonate → 4-(4-Chloromethyl-phenylmethoxy)-2-isopropylidenecoumaran-3-one

HRID 381682Notes

Reaction equation

HRID 381682 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10](=[O:20])[C:11](=[C:17]([CH3:19])[CH3:18])[O:12]2.[Cl:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]Cl)=[CH:25][CH:24]=1>CC(=O)CC>[Cl:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][O:7][C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[C:10](=[O:20])[C:11](=[C:17]([CH3:18])[CH3:19])[O:12]3)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12171alpha,alpha'-Dichloro-p-xyleneHCID 183638364-Hydroxy-2-(propan-2-ylidene)-1-benzofuran-3(2H)-one

Product 1

HCID 183638384-(4-Chloromethyl-phenylmethoxy)-2-isopropylidenecoumaran-3-oneYield 19.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2.8 g Potassium carbonate is added over 3 hours to a mixture of 3.8 g 4-hydroxy-2-isopropylidenecoumaran-3-one, 3.5 g 1,4-bis-(chloromethyl)benzene and 150 ml butanone at 70-75° C. The mixture is refluxed for 16 hours, then filtered, the filtrate evaporated and the residue purified by silica gel chromatography (eluent isohexane/ethyl acetate 3:1) to give 1.3 g of the desired intermediate.

Workup

  1. temperatureThe mixture is refluxed for 16 hours
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. customthe residue purified by silica gel chromatography (eluent isohexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-1d37f4c1fabe496b92c3eb3b31ef3485
Source dataset
uspto-grants-2001_10
Patent number
US06307051B1

Reaction notes

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