Triethylamine → 4-(1-Monofluoro-2-decyloxycarbonyl)phenyl 4-octyloxybenzoate

HRID 247781

Reaction equation

HRID 247781 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([O:8][CH:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][F:11])=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:29]([O:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C(Cl)Cl.O>[CH2:29]([O:37][C:38]1[CH:39]=[CH:40][C:41]([C:42]([O:1][C:2]2[CH:21]=[CH:20][C:5]([C:6]([O:8][CH:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][F:11])=[O:7])=[CH:4][CH:3]=2)=[O:43])=[CH:45][CH:46]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27602504-Octyloxybenzoyl chlorideHCID 190138911-Monofluoro-2-decyl 4-hydroxybenzoate2×

Product 1

HCID 190139064-(1-Monofluoro-2-decyloxycarbonyl)phenyl 4-octyloxybenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the 1-monofluoro-2-decyl 4-hydroxybenzoate prepared in (1) (0.1 g) and triethylamine (0.04 g) in methylene chloride (10 ml) was slowly added under ice cooling a solution of 4-n-octyloxybenzoic acid chloride (0.1 g) in methylene chloride (10 ml). The mixture was left to stand until it reached room temperature and stirred overnight. The mixture was poured in water and extracted with methylene chloride. The extracted layer was washed with dilute aqueous hydrochloric acid solution, water, 1N aqueous sodium carbonate solution and water, in this order, and dehydrated over anhydrous magnesium sulfate. After the solution was distilled under reduced pressure to remove the solvent, the product was purified by silica-gel column chromatography to obtain the titled compound (0.13 g).

Workup

  1. waitThe mixture was left
  2. customreached room temperature
  3. extractionextracted with methylene chloride
  4. washThe extracted layer was washed with dilute aqueous hydrochloric acid solution, water, 1N aqueous sodium carbonate solution and water, in this order
  5. distillationAfter the solution was distilled under reduced pressure
  6. customto remove the solvent
  7. customthe product was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-0a33a91ca3894683ad8fb3ad64b66b95
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Linked notes

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