Acetic Acid → 7-(4-Hydroxyphenyl)heptanoic acid

HRID 36128Notes

Reaction equation

HRID 36128 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:5][CH:4]=1.Br.C(O)(=O)C>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 10728520HCID 10728520, compound

Product 1

HCID 148220177-(4-Hydroxyphenyl)heptanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 ml single-neck flask was charged with 7-(4-methoxyphenyl)heptanoic acid (A3) (20.0 g, 90 mmole), freshly distilled 48% hydrobromic acid (80 ml), and glacial acetic acid (40 ml). The mixture was heated to reflux by immersing the flask in an oil bath regulated at 140° C. for 3.5 hours. At the end of this time, water (80 ml) was added, the flask was cooled to room temperature, and placed in the refrigerator overnight. The resulting solid, 7-(4-hydroxyphenyl)heptanoic acid, was collected by suction filtration, washed with water (2×80 ml), and dried in vacuo. The product was of sufficient purity to be used in the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customplaced in the refrigerator overnight
  4. filtrationThe resulting solid, 7-(4-hydroxyphenyl)heptanoic acid, was collected by suction filtration
  5. washwashed with water (2×80 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-0e3cb3a69ac84c848e1db164e04306d1
Source dataset
uspto-grants-1995_05
Patent number
US05412144

Reaction notes

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