Hydrochloric Acid → HCID 178516057, compound

HRID 1937272Notes

Reaction equation

HRID 1937272 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:11]2[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)[CH:7]=[CH:8][C:9]=1[OH:10].Cl.O>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]([C@H:11]2[CH2:12][CH2:13][C@H:14]([OH:17])[CH2:15][CH2:16]2)[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 22460228HCID 22460228, compound

Product 1

HCID 178516057HCID 178516057, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

0.76 g (20 mmols) NaBH4 was suspended in 30 ml THF under nitrogen and cooled to 0° C. A solution of 4.16 g 4-(3-fluoro-4-hydroxyphenyl)cyclohexanone in 50 ml THF was added dropwise at the same temperature over a period of 15 minutes, and the resulting mixture was stirred at 0° C. until no more of the starting material was present. 10 ml 25% HCl was then added dropwise at a temperature of between 0-10° C., and stirred for a further 30 minutes. The reaction mixture was then poured into 100 ml of water and extracted three times with 50 ml of diethyl ether. The combined organic phases were washed twice with 50 ml of water, dried over magnesium sulphate and filtered. Removal of the solvent and recrystallisation of the residue from isopropanol gave 2-fluoro-4-(trans-4-hydroxycyclohexyl)phenol.

Workup

  1. stirringstirred for a further 30 minutes
  2. extractionextracted three times with 50 ml of diethyl ether
  3. washThe combined organic phases were washed twice with 50 ml of water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customRemoval of the solvent and recrystallisation of the residue from isopropanol

Sources & evidence

ORD record
ord-e75ee0eeca0e42ec93f6c1a34acec421
Source dataset
uspto-grants-2002_05
Patent number
US06395351B1

Reaction notes

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