p-Toluenesulfonic acid monohydrate → 2-Hydroxy-5-octadec-1-enylbenzoic acid

HRID 615486Notes

Reaction equation

HRID 615486 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([CH:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 13393461HCID 13393461, compound

Product 1

HCID 542110462-Hydroxy-5-octadec-1-enylbenzoic acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Hydroxy-5-(1-hydroxyoctadecyl)benzoic acid (100 mg) was dissolved in 20 ml of benzene and a trace of p-toluenesulfonic acid monohydrate added. The solution was refluxed for 10 minutes, then 10 ml of solvent was distilled. Reflux was continued for about 18 hours. Upon cooling to room temperature, the solution was extracted with 1% sodium bicarbonate solution and the solvent removed under a stream of nitrogen gas to give crystals. The material was recrystallized from methanol to give the title compound, m.p. ca. 95° C. ##STR11##

Workup

  1. temperatureThe solution was refluxed for 10 minutes
  2. distillation10 ml of solvent was distilled
  3. temperatureReflux
  4. extractionthe solution was extracted with 1% sodium bicarbonate solution
  5. customthe solvent removed under a stream of nitrogen gas
  6. customto give crystals
  7. customThe material was recrystallized from methanol

Sources & evidence

ORD record
ord-6ef1c31af6ab4b2ead4e4b0c12d925aa
Source dataset
uspto-grants-1985_02
Patent number
US04499295

Reaction notes

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