Hydrochloric Acid → HCID 70078910, compound

HRID 1291839Notes

Reaction equation

HRID 1291839 reaction equation
[OH:1][C:2]1([C:14](O)=[O:15])[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH2:3]1.C(OCC)(=O)C.O.Cl>O1CCCC1>[OH:1][C:2]1([CH2:14][OH:15])[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 66911356HCID 66911356, compound

Product 1

HCID 70078910HCID 70078910, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxy-4-biphenylcarboxylic acid (2.14 g) in tetrahydrofuran (25 ml) under an argon atmosphere was added slowly 1M borane-THF complex (50 ml). The resulting mixture was stirred for 18 hours before the addition of ethyl acetate (10 ml) and water (100 ml). The resulting mixture was acidified with 2N hydrochloric acid and stirred for 30 minutes. The aqueous layer was extracted with ethyl acetate (2×100 ml). The organic extracts were combined, dried (MgSO4) and evaporated. Recrystallisation from a small volume of ethyl acetate gave 4-hydroxy-4-biphenylmethanol (580 mg): NMR (d6DMSO), δ 4.5(s,2H), 6.85(d,2H), 7.35(d,2H), 7.45-7.55(dd,4H), 9.45(s,1H); m/e 201(M+H)+.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (2×100 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customRecrystallisation from a small volume of ethyl acetate

Sources & evidence

ORD record
ord-17815b28b47645309b0a39c8ffe5b529
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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