Trifluoroacetic acid → 15-Methyl-3-(13-methyltetradecanoyloxy)hexadecanoic acid

HRID 236471Notes

Reaction equation

HRID 236471 reaction equation
[CH3:1][CH:2]([CH3:40])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([O:23][C:24](=[O:39])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH2:15][C:16]([O:18]C(C)(C)C)=[O:17].FC(F)(F)C(O)=O>>[CH3:1][CH:2]([CH3:40])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([O:23][C:24](=[O:39])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH2:15][C:16]([OH:18])=[O:17]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20216763HCID 20216763, compound

Product 1

HCID 2021675515-Methyl-3-(13-methyltetradecanoyloxy)hexadecanoic acidYield 88.8%

Procedure

To tert-butyl 15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoate (500 mg) was added trifluoroacetic acid (5 ml) and the mixture was stirred at ambient temperature for 2 hours. Excess trifluoroacetic acid was distilled off under reduced pressure. Dry benzene was added to the residue and the solvent was evaporated off. This operation was repeated three times. The residue was dried up by using high vacuum pump to afford an oil of 15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoic acid (400 mg).

Workup

  1. distillationExcess trifluoroacetic acid was distilled off under reduced pressure
  2. additionDry benzene was added to the residue
  3. customthe solvent was evaporated off
  4. customThe residue was dried up

Sources & evidence

ORD record
ord-93ec6e7a43f64f66aaf11a958f9c5bef
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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