Acetic Acid → Benzenenonanoic acid, 4-hydroxy-

HRID 1723413Notes

Reaction equation

HRID 1723413 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][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[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][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 14555669HCID 14555669, compound

Product 1

HCID 10422225Benzenenonanoic acid, 4-hydroxy-Yield 60.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 55.7 gms 9(4-methoxyphenyl)nonanoic acid, 640 ml 48% HBr and 640 ml acetic acid was refluxed for 7 hours and cooled to room temperature overnight. The solution was diluted with a large excess of water, whereupon a solid precipitated. The solid was filtered off, re-suspended in water, and filtered again. It was dissolved in ether, washed four times with water, and the organic phase was dried over MgSO4 overnight. The drying agent was filtered off and the solvent removed in vacuo to give a solid which was recrystallized from toluene to give 31.8 gms (58%) 9(4-hydroxyphenyl)nonanoic acid, m.p. 103°-5°.

Workup

  1. temperaturewas refluxed for 7 hours
  2. customwhereupon a solid precipitated
  3. filtrationThe solid was filtered off
  4. filtrationfiltered again
  5. dissolutionIt was dissolved in ether
  6. washwashed four times with water
  7. dry with materialthe organic phase was dried over MgSO4 overnight
  8. filtrationThe drying agent was filtered off
  9. customthe solvent removed in vacuo
  10. customto give a solid which
  11. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-30cda53a75ba4ca38aced03f36913cb1
Source dataset
uspto-grants-1989_08
Patent number
US04861798

Reaction notes

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