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

HRID 1679646Notes

Reaction equation

HRID 1679646 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>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

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen Bromide2×HCID 202878722-(3,5-Dimethoxyphenyl)-5-(p-fluorophenyl)pentane

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-(4-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 bromide gas (approximately 1/2 hour). The reaction 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-(4-fluorophenyl)pentane 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-(4-fluorophenyl)pentane as a brown oil which distills at 180°/0.01 mmHg

Sources & evidence

ORD record
ord-eff53fe8c3d0496fbae8b87c702ac154
Source dataset
uspto-grants-1978_03
Patent number
US04081449

Reaction notes

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