p-Toluenesulfonic acid → HCID 178476592, compound

HRID 330554Notes

Reaction equation

HRID 330554 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:4][CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>>[C:27]([O:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:6][CH2:7]1)(=[O:29])[CH3:28]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 178525432HCID 178525432, compound

Product 1

HCID 178476592HCID 178476592, compoundYield 82%

Procedure

trans-6-(4-Hydroxycyclohexyl)hexanoic acid (5 g) is dissolved in acetic anhydride (25 ml), and p-toluenesulfonic acid (10 mg) is added to the solution. The mixture is stirred at 60° to 70° C. for an hour. The excess acetic anhydride is distilled off under reduced pressure and, after addition of water, the mixture is stirred at room temperature for 24 hours and then at 50° to 60° C. for further 5 hours and poured into ice-water. The resulting crystalline precipitate is recrystallized from ethanol-water to give 4.93 g (82%) of trans-6-(4-acetoxycyclohexyl)hexanoic acid as colorless needles, m.p. 82°-86° C.

Workup

  1. distillationThe excess acetic anhydride is distilled off under reduced pressure
  2. additionafter addition of water
  3. stirringthe mixture is stirred at room temperature for 24 hours
  4. additionpoured into ice-water
  5. customThe resulting crystalline precipitate is recrystallized from ethanol-water

Sources & evidence

ORD record
ord-733a7ba9c33d4bf5b6af23c2e4476168
Source dataset
uspto-grants-1990_01
Patent number
US04897420

Reaction notes

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