Potassium Hydroxide → HCID 54286269, compound

HRID 620325Notes

Reaction equation

HRID 620325 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([C@@H:8]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=[O:19])[CH2:9][N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[BH4-].[Na+]>O.CO.CCOCC.CCCCC>[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([C@@H:8]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[OH:19])[CH2:9][N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 4311764Sodium borohydrideHCID 54230375HCID 54230375, compound

Product 1

HCID 54286269HCID 54286269, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent3×HCID 21877078Diethylether pentaneSolvent

Procedure

A solution of 6.8 g (121 mmol) of potassium hydroxide in 40 ml of water is added dropwise while cooling within about 30 minutes to a solution of 28.2 g (100 mmol) of rac-(2S*)-2-[(R*)-4-chloro-α-(nitromethyl)benzyl]cyclohexanone in 200 ml of methanol so that the temperature does not exceed 5°. An ice-cold solution of 2.85 g (75 mmol) of sodium borohydride in 20 ml of water is subsequently added dropwise, whereupon the mixture is stirred at 0° for 3 hours. After treatment with 12 ml of acetic acid the solvent is distilled off. The residue obtained is treated with water, whereupon the mixture is extracted twice with 200 ml of ether each time. The organic phase is washed with water, dried over magnesium sulphate and evaporated. The oil obtained is taken up in ether/pentane, left to stand in a refrigerator and the crystalline product obtained is recrystallized from ether/hexan. There is obtained rac-(1S*)-2-[(R*)-4-chloro-α-(nitromethyl)benzyl]cyclohexanol of m.p. 82°-84°.

Workup

  1. customdoes not exceed 5°
  2. distillationAfter treatment with 12 ml of acetic acid the solvent is distilled off
  3. customThe residue obtained
  4. extractionis extracted twice with 200 ml of ether each time
  5. washThe organic phase is washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe oil obtained
  9. waitleft
  10. customthe crystalline product obtained
  11. customis recrystallized from ether/hexan

Sources & evidence

ORD record
ord-e060ca366d184660995e999c55e114dc
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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