2-Chloro-1-(3,4,5-trimethoxyphenyl)ethan-1-one → HCID 53765629, compound

HRID 258229Notes

Reaction equation

HRID 258229 reaction equation
ClCC(C1C=CC(OC)=C(OC)C=1OC)=O.[Cl:17][CH2:18][C:19]([C:21]1[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=1)=[O:20]>C(OCC)(=O)C>[Cl:17][CH2:18][CH:19]([C:21]1[CH:22]=[C:23]([O:31][CH3:32])[C:24]([O:29][CH3:30])=[C:25]([O:27][CH3:28])[CH:26]=1)[OH:20]

Participants

4

Reactant 2

HCID 127899762-Chloro-1-(3,4,5-trimethoxyphenyl)ethan-1-oneHCID 23197733HCID 23197733, compound

Product 1

HCID 53765629HCID 53765629, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Cultivation and reaction were carried out in the same way as described in Example 9 except that 2-chloro-1-(2',3',4'-trimethoxyphenyl) ethanone, 2-chloro-1-(3',4',5'-trimethoxyphenyl) ethanone were used as substrate and after completion of reaction, extraction was done twice using 300 ml of ethyl acetate. After dehydration of the ethyl acetate layer, the solvent was removed under reduced pressure, the resulting oily substance was refined by silica gel chromatography (hexane/ethyl acetate=7/1) and (-)-2-chloro-1-(2',3',4'-trimethoxyphenyl) ethanol, (-)-2-chloro-1-(3',4',5'-trimethoxyphenyl) ethanol were obtained. Their yield and specific rotation were as shown in Table 11.

Workup

  1. customCultivation and reaction
  2. customafter completion of reaction, extraction
  3. customAfter dehydration of the ethyl acetate layer, the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-166a0c0fa1ee440ba4bc3ae5440f2937
Source dataset
uspto-grants-1993_11
Patent number
US05266485

Reaction notes

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