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

HRID 2057993Notes

Reaction equation

HRID 2057993 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-34d661c9284a49988485ce1647c2eb49
Source dataset
uspto-grants-1980_07
Patent number
US04214004

Reaction notes

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