Hydrochloric Acid → 2'-Fluoro-5-methyl-1,2,3,6-tetrahydro[1,1'-biphenyl]-3-ol

HRID 1995111Notes

Reaction equation

HRID 1995111 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:15][C:14](=[O:16])[CH:13]=[C:12]([CH3:17])[CH2:11]1.Cl>C(O)C>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:15][CH:14]([OH:16])[CH:13]=[C:12]([CH3:17])[CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydride3×HCID 12853039HCID 12853039, compound

Product 1

HCID 128530402'-Fluoro-5-methyl-1,2,3,6-tetrahydro[1,1'-biphenyl]-3-olYield 95.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred mixture of sodium borohydride (2.0 g, 0.05 mole) in 400 ml of ethanol was added in one portion 5-(2-fluorophenyl)-3-methyl-2-cyclohexen-1-one (42.3 g, 0.21 mole) in 50 ml of ethanol. The reaction mixture was heated under reflux for 16 hours. An additional 2.0 g of sodium borohydride was then added to the reaction mixture and heating under reflux continued for an additional 2 hours. Again, 2.0 g of sodium borohydride was added to the reaction mixture and heating under reflux continued for a 2 hour period. The reaction mixture was stirred with ice, then acidified with aqueous 10% hydrochloric acid. The mixture was extracted with diethyl ether, and the ether extract was washed with an aqueous solution saturated with sodium bicarbonate. The organic layer was dried with sodium sulfate and filtered. The filtrate was evaporated under reduced pressure to give 5-(2-fluorophenyl)-3-methyl-2-cyclohexen-1-ol (41.2 g) as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 16 hours
  3. temperatureheating
  4. temperatureunder reflux
  5. temperatureheating
  6. temperatureunder reflux
  7. waitcontinued for a 2 hour period
  8. extractionThe mixture was extracted with diethyl ether
  9. extractionthe ether extract
  10. washwas washed with an aqueous solution saturated with sodium bicarbonate
  11. dry with materialThe organic layer was dried with sodium sulfate
  12. filtrationfiltered
  13. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0ddacd702941498a83fd5f2e1fc5cafd
Source dataset
uspto-grants-1983_09
Patent number
US04402973

Reaction notes

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