22-Linoleoyloxydocosanoic Acid, Tert.-Butyl Ester → 22-Linoleoyloxydocosanic Acid

HRID 2399986Notes

Reaction equation

HRID 2399986 reaction equation
[C:1]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]([O:44]C(C)(C)C)=[O:43])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>C1C=CC=CC=1>[C:1]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]([OH:44])=[O:43])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 1

HCID 8674900122-Linoleoyloxydocosanoic Acid, Tert.-Butyl Ester

Product 1

HCID 8674900222-Linoleoyloxydocosanic Acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of the ester (35) (0.15 g, 0.222 mmol) in dry benzene (3 ml) under nitrogen was treated with a catalytic amount of toluenesuphonic acid and the resulting solution heated at reflux for 5 hours, after which time no starting material remained on tlc. The volatile components were removed in vacuo and the residue chromatographed on silica (5 g). Elution with 10% ether in petrol gave the title compound (42) as a white wax (0.1 g, 73%).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for 5 hours
  3. customThe volatile components were removed in vacuo
  4. customthe residue chromatographed on silica (5 g)
  5. washElution with 10% ether in petrol

Sources & evidence

ORD record
ord-79423960b06f46dca3827ccee3a1c9a5
Source dataset
uspto-grants-1995_09
Patent number
US05451691

Reaction notes

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