Sodium Hydroxide → Biphenyl

HRID 1655144Notes

Reaction equation

HRID 1655144 reaction equation
[OH-].[Na+].C[C@@H](CC)CC[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16](O)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1>C(O)C>[C:10]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:11]=[CH:12][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13685076HCID 13685076, compound

Product 1

HCID 7095Biphenyl

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.8 g of sodium hydroxide is dissolved in a solution of 5.09 g of 4'-[(S)-3-methylpentyl]-4-biphenylol (EP-A-131373) in 40 ml of ethanol. The solution is treated with 6.26 g of (S)-2-octyl-p-toluenesulfonate and heated to boiling for 6 hours. Subsequently, the solvent is distilled off and the residue is taken up in 100 ml of diethyl ether and 50 ml of 0.5 N hydrochloric acid. The aqueous phase is separated and back-extracted with 50 ml of diethyl ether. The combined organic phase is washed in succession with 50 ml of water, with 30 ml of 3 N sodium hydroxide solution and three times with 50 ml of water each time, then dried over sodium sulfate and concentrated. Crystallization of the residue from ethanol gives 4-[(R)-1-methylheptyloxy]-4'-(S)-3-methylpentyl]biphenyl, m.p. (C-I) 12° C.

Workup

  1. temperatureheated
  2. distillationSubsequently, the solvent is distilled off
  3. customThe aqueous phase is separated
  4. extractionback-extracted with 50 ml of diethyl ether
  5. washThe combined organic phase is washed in succession with 50 ml of water, with 30 ml of 3 N sodium hydroxide solution and three times with 50 ml of water each time
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customCrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-458fd640baac4585b897f5aaa055748d
Source dataset
uspto-grants-1993_10
Patent number
US05250222

Reaction notes

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