p-Toluenesulfonic acid → HCID 178476591, compound

HRID 330558Notes

Reaction equation

HRID 330558 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][CH2:13][C:14]([OH:16])=[O:15])[CH2:4][CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>>[C:28]([O:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH2:6][CH2:7]1)(=[O:30])[CH3:29]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 178525427HCID 178525427, compound

Product 1

HCID 178476591HCID 178476591, compound

Procedure

trans-7-(4-Hydroxycyclohexyl)heptanoic acid (6.5 g) and p-toluenesulfonic acid (15 mg) are stirred in acetic anhydride (32.5 ml) at 60°-70° C. for 1.5 hours. The excess acetic anhydride is distilled off under reduced pressure, followed by addition of water (90 ml), and the mixture is stirred for 3 days. The resulting crystalline precipitate is collected by filtration and recrystallized from ethyl acetate-hexane to give 6.5 g of trans-7-(4-acetoxycyclohexyl)heptanoic acid as colorless needless, m.p. 66°-68° C.

Workup

  1. distillationThe excess acetic anhydride is distilled off under reduced pressure
  2. additionfollowed by addition of water (90 ml)
  3. filtrationThe resulting crystalline precipitate is collected by filtration
  4. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1803b147b0aa45b59d73d57cad328eb5
Source dataset
uspto-grants-1990_01
Patent number
US04897420

Reaction notes

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