Acetic Acid → 5-[5-(4-Fluorophenyl)pentan-2-yl]benzene-1,3-diol

HRID 1580168Notes

Reaction equation

HRID 1580168 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:11]([CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:12])[CH:6]=[C:7]([O:9]C)[CH:8]=1.C(O)(=O)C.Br.[H][H]>O>[OH:2][C:3]1[CH:4]=[C:5]([CH:11]([CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[CH3:12])[CH:6]=[C:7]([OH:9])[CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 202878722-(3,5-Dimethoxyphenyl)-5-(p-fluorophenyl)pentaneHCID 178418361HCID 178418361, compound

Product 1

HCID 202879045-[5-(4-Fluorophenyl)pentan-2-yl]benzene-1,3-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Fifty grams of the above-prepared 2-(3,5-dimethoxyphenyl)-5-(p-fluorophenyl)pentane, 450 ml. of acetic acid and 180 ml. of 48% HBr in water were mixed. While cooling, the mixture was saturated with hydrogen gas (approximately one-half hour). The reacion was placed in an 87° bath and stirred for 17 hours. The reaction was then concentrated in vacuo and the residue neutralized with K2CO3 and NaHCO3, extracted with ether, treated with charcoal and MgSO4 and filtered to yield 45 g. of 2-(3,5-dihydroxyphenyl)-5-(-p-fluorophenylpentane as a brown oil which distills at 180°/0.01 mmHg.

Workup

  1. temperatureWhile cooling
  2. customwas placed in an 87°
  3. concentrationThe reaction was then concentrated in vacuo
  4. extractionextracted with ether
  5. additiontreated with charcoal and MgSO4
  6. filtrationfiltered
  7. customto yield 45 g
  8. distillationof 2-(3,5-dihydroxyphenyl)-5-(-p-fluorophenylpentane as a brown oil which distills at 180°/0.01 mmHg

Sources & evidence

ORD record
ord-170d3b28e93648b2a076293eff65af03
Source dataset
uspto-grants-1976_01
Patent number
US03932432

Reaction notes

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