Sodium Hydroxide → 6-(2-Chlorophenyl)-6-hydroxy-2-cyclohexen-1-one

HRID 1655673Notes

Reaction equation

HRID 1655673 reaction equation
N([O-])=O.[Na+].N[C:6]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:11](=[O:12])[CH:10]=[CH:9][CH2:8][CH2:7]1.[OH-:20].[Na+]>O.Cl>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:6]1([OH:20])[C:11](=[O:12])[CH:10]=[CH:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 162835DehydronorketamineHCID 23668193Sodium Nitrite

Product 1

HCID 134679466-(2-Chlorophenyl)-6-hydroxy-2-cyclohexen-1-oneYield 28%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Sodium nitrite (16 mg, 0.23 mmol) in water (0.5 ml) was added to a stirred solution of 6-amino-6-(2-chlorophenyl)-2-cyclohexen-1-one (50 mg, 0.23 mmol) in 1/3N HCl (1.5 ml) at 0° C. After 1 h the reaction was neutralized with sodium hydroxide and allowed to warm to room temperature for 30 minutes. The reaction was partitioned between saturated bicarbonate and ethyl acetate, the organic phase was washed with brine, dried (Na2SO4), and the solvent removed by evaporation. Purification was achieved by preparative thin layer chromatography on silica gel eluting with 3:2 ethyl acetate/hexane. Isolation of the UV active band at Rf 0.7 gave 6-(2-Chlorophenyl)-6-hydroxy-2-cyclohexen-1-one (14.2 mg, 28%).

Workup

  1. customThe reaction was partitioned between saturated bicarbonate and ethyl acetate
  2. washthe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed by evaporation
  5. customPurification

Sources & evidence

ORD record
ord-3379f0032a68426fad26fdfdb598b6fd
Source dataset
uspto-grants-1993_10
Patent number
US05250732

Reaction notes

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