Tert-butyl 3-hexadecanoyloxyoctadecanoate → 3-Hexadecanoyloxyoctadecanoic acid

HRID 236476

Reaction equation

HRID 236476 reaction equation
[C:1]([O:18][CH:19]([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][CH3:42])[CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>FC(F)(F)C(O)=O>[C:1]([O:18][CH:19]([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][CH3:42])[CH2:20][C:21]([OH:23])=[O:22])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 1

HCID 20216792Tert-butyl 3-hexadecanoyloxyoctadecanoate

Product 1

HCID 134890283-Hexadecanoyloxyoctadecanoic acidYield 88.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To tert-butyl 3-hexadecanoyloxyoctadecanoate (156 g) was added trifluoroacetic acid (200 ml) at 0° C. After the temperature of the mixture was reached to ambient temperature, the resulting solution was allowed to stand at the same temperature for 3 hours. Excess trifluoroacetic acid was distilled off under reduced pressure. The residue was taken up in benzene and the solvent was evaporated off. This operation was repeated twice to remove trifluoroacetic acid completely. The residue was recrystallized from petroleum ether in refrigerator to afford crystals of 3-hexadecanoyloxyoctadecanoic acid (125 g).

Workup

  1. customwas reached to ambient temperature
  2. distillationExcess trifluoroacetic acid was distilled off under reduced pressure
  3. customthe solvent was evaporated off
  4. customto remove trifluoroacetic acid completely
  5. customThe residue was recrystallized from petroleum ether in refrigerator

Sources & evidence

ORD record
ord-fb118060bea84f088a0355de05b73f24
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Linked notes

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