Dichloromethane → HCID 67550038, compound

HRID 2214317Notes

Reaction equation

HRID 2214317 reaction equation
C(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C@H:16]([CH3:21])[CH2:17][C:18](Cl)=[O:19])[CH:13]=[CH:14][CH:15]=1.C([C@H:25]1[CH2:30][CH2:29][C@H:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:27][CH2:26]1)CC>O>[CH:31]1([C:28]2[CH:27]=[CH:26][C:25]([C:18](=[O:19])[CH2:17][C@H:16]([C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH3:8])[CH:11]=3)[CH3:21])=[CH:30][CH:29]=2)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

6

Reactant 4

HCID 6344Dichloromethane3×HCID 6451240Aluminum(III) ChlorideHCID 87905706HCID 87905706, compoundHCID 178447856HCID 178447856, compound

Product 1

HCID 67550038HCID 67550038, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a methylene chloride suspension of aluminum chloride, a methylene chloride solution of (R)-3-(3-methoxyphenyl)butyric acid chloride was added dropwise under ice cooling. After stirring at the same temperature for 15 minutes, a methylene chloride solution of trans-4-propylcyclohexylbenzene was added dropwise. After the completion of the reaction, the reaction system was added to iced water and the organic layer was separated by adding methylene chloride. The organic layer was washed twice with water and then washed with saturated brine. The aqueous layer was washed with methylene chloride and, after combining the organic layer, the solvent was concentrated to obtain a crude product of (R)-1-(4-cyclohexylphenyl)-3-(3-methoxyphenyl)-butan-1-one. The resulting crude product was purified by column chromatography and recrystallized from ethanol to obtain (R)-1-(4-cyclohexylphenyl)-3-(3-methoxyphenyl)-butan-1-one (R-isomer of the compound represented by the formula (XI-c)).

Workup

  1. customAfter the completion of the reaction
  2. customthe organic layer was separated
  3. additionby adding methylene chloride
  4. washThe organic layer was washed twice with water
  5. washwashed with saturated brine
  6. washThe aqueous layer was washed with methylene chloride
  7. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-2cec827d36324b1285c3dc6dd2395ba5
Source dataset
uspto-grants-2006_09
Patent number
US07108896B2

Reaction notes

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