p-Toluenesulfonic acid → HCID 14324678, compound

HRID 373477Notes

Reaction equation

HRID 373477 reaction equation
[CH3:1][C:2]1[C:6]([CH3:8])([CH3:7])[CH2:5][CH2:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11].[C:13]1(C)C=CC(S(O)(=O)=O)=C[CH:14]=1>C(O)C>[CH2:13]([O:11][C:10](=[O:12])[CH2:9][C:3]1[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[C:2]=1[CH3:1])[CH3:14]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 123023511-Cyclopentene-1-acetic acid, 2,3,3-trimethyl-

Product 1

HCID 14324678HCID 14324678, compoundYield 745.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

A solution of β-campholenic acid (10 g) and p-toluene-sulfonic acid (1 g) in ethanol (500 ml) was kept at reflux (78° C.) for 5 hours, while the condensate was perculated through a layer of molecular sieves (3 Å) (40 g). The alcohol was then removed, the residue taken up in CH2Cl2 (500 ml) and the solution extracted with ice cold 5% aqueous sodium hydroxide (500 ml) and water (2×500 ml). Concentration of the dried CH2Cl2 solution gave a crude oil (12 g) which was distilled through a 3" Vigreux column to give 8.5 g of a colorless liquid; bp 58° C. @ 0.8 mm Hg; analysis: (CW 20M fused silica column, 120°-190° C.; 5° C./min.) 96% ethyl β-campholenate; odor: fruity, berry, resinous; flavor: fruity, woody, winey, berry.

Workup

  1. customThe alcohol was then removed
  2. extractionthe solution extracted with ice cold 5% aqueous sodium hydroxide (500 ml) and water (2×500 ml)
  3. customConcentration of the dried CH2Cl2 solution gave a crude oil (12 g) which
  4. distillationwas distilled through a 3" Vigreux column

Sources & evidence

ORD record
ord-caeb4df3bf4c46c09f96c75bb9339d43
Source dataset
uspto-grants-1992_11
Patent number
US05164364

Reaction notes

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