Dicyclohexylcarbodiimide → 4-Undecanoyloxybenzoic acid

HRID 247790

Reaction equation

HRID 247790 reaction equation
[C:1]([O:12][C:13]1[CH:43]=[CH:42][C:16]([C:17]([O:19]C2C=CC(C(OC(CCCCCCCC)C(F)(F)F)=O)=CC=2)=[O:18])=[CH:15][CH:14]=1)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].O[C:45]1C=CC(C(OC(CCCCCCCC)C(F)(F)F)=O)=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>O1CCCC1>[C:1]([O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:42][CH:43]=1)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:45]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 147457541,1,1-Trifluoro-2-decyl 4-hydroxybenzoateHCID 190139204-(1,1,1-Trifluoro-2-decyloxycarbonyl)phenyl 4-n-decanoyloxybenzoate

Product 1

HCID 154568744-Undecanoyloxybenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 4-undecanoyloxybenzoic acid )0.3 g) obtained in (1) above and the 1,1,1-trifluoro-2-decyl-4-hydroxybenzoate (0.3 g) obtained in Example 12, (2) in tetrahydrofuran (about 30 ml) were added dicyclohexylcarbodiimide (0.25 g) and dimethylaminopyridine (0.01 g). The mixture was stirred at room temperature for about 20 hours. The solution was distilled to remove the solvent and the residue was dissolved in dichloromethane and washed with water. The organic layer was dried over anhydrous magnesium sulfate and was distilled to remove the solvent. The residue was purified by silica-gel column chromatography (developer : hexane/ethyl acetate=20/1) to obtain the titled compound (0.21 g).

Workup

  1. distillationThe solution was distilled
  2. customto remove the solvent
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationwas distilled
  7. customto remove the solvent
  8. customThe residue was purified by silica-gel column chromatography (developer : hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-d4f4dcd3467640efad5080b248df6aa7
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Linked notes

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