Sodium Chloride → HCID 22155919, compound

HRID 1074158Notes

Reaction equation

HRID 1074158 reaction equation
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14].[Cl-].[Na+]>CCOCC>[C:1]1([C:13]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)([OH:14])[CH2:12][CH2:11][CH2:10][Cl:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 2535334-ChlorobutyrophenoneHCID 178478990HCID 178478990, compound

Product 1

HCID 22155919HCID 22155919, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred and ice-cooled solution of cyclohexyl magnesium chloride (60 mmol) in dry ether (23.2 ml), 4-chlorobutyrophenone (5.5 g) in ether (17 ml) was added dropwise. The mixture was stirred at 0° C. for 2 hours, then an aqueous solution of sodium chloride was cautiously added. The organic phase was separated and dried. The solvent was removed and the residue was purified by column chromatography (hexane, ether 98:2), affording 5 g of 1-phenyl-1-cyclohexyl-4-chloro-1-butanol as an oil.

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at 0° C. for 2 hours
  3. customThe organic phase was separated
  4. customdried
  5. customThe solvent was removed
  6. customthe residue was purified by column chromatography (hexane, ether 98:2)

Sources & evidence

ORD record
ord-cc371f91197842349a7a4f2dbd974ab6
Source dataset
uspto-grants-1990_11
Patent number
US04973592

Reaction notes

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