Tert-butyl 3-hexadecanoyloxyoctadecanoate → 3-Hexadecanoyloxyoctadecanoic acid

HRID 236491Notes

Reaction equation

HRID 236491 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 108%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To tert-butyl 3-hexadecanoyloxyoctadecanoate (16.56 g) was added trifluoroacetic acid (20 ml) and the mixture was stirred at room temperature for 1 hour. Trifluoroacetic acid was removed off under reduced pressure, and to the residue was added dry benzene, followed by evaporation of the solvent. This operation was repeated three times. To a solution of the dried residue in ethyl acetate (250 ml) were added N-hydroxysuccinimide (3.21 g) and N,N'-dicyclohexylcarbodiimide (5.75 g). The mixture was stirred at ambient temperature overnight and then filtered to remove N,N'-dicyclohexylurea. The filtrate was condensed and dried up by high vacuum pump to give N-hydroxysuccinimide ester of 3-hexadecanoyloxyoctadecanoic acid (16.2 g).

Workup

  1. customTrifluoroacetic acid was removed off under reduced pressure
  2. additionto the residue was added dry benzene
  3. customfollowed by evaporation of the solvent
  4. additionTo a solution of the dried residue in ethyl acetate (250 ml) were added N-hydroxysuccinimide (3.21 g) and N,N'-dicyclohexylcarbodiimide (5.75 g)
  5. stirringThe mixture was stirred at ambient temperature overnight
  6. filtrationfiltered
  7. customto remove N,N'-dicyclohexylurea
  8. customcondensed
  9. customdried up by high vacuum pump

Sources & evidence

ORD record
ord-64af87270a6c464ea0ae488346096952
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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