Triethylamine → 4-[[4'-(Octyloxy)-4-biphenylyl]carbonyloxy]benzoic acid 1-(trifluoromethyl)heptyl ester

HRID 247778Notes

Reaction equation

HRID 247778 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([O:8][CH:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:10]([F:13])([F:12])[F:11])=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:29]([O:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][C:47]([C:50](Cl)=[O:51])=[CH:46][CH:45]=2)=[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:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][C:47]([C:50]([O:1][C:2]3[CH:3]=[CH:4][C:5]([C:6]([O:8][CH:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:10]([F:11])([F:12])[F:13])=[O:7])=[CH:20][CH:21]=3)=[O:51])=[CH:46][CH:45]=2)=[CH:40][CH:39]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 110784734-(4-Octyloxyphenyl)benzoyl chlorideHCID 145492151,1,1-Trifluoro-2-octyl 4-hydroxybenzoate

Product 1

HCID 147669654-[[4'-(Octyloxy)-4-biphenylyl]carbonyloxy]benzoic acid 1-(trifluoromethyl)heptyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of the 1,1,1-trifluoro-2-octyl 4-hydroxybenzoate prepared above (0.53 g) and triethylamine (0.18 g) in methylene chloride (10 ml) was slowly added c under ice cooling a solution of 4-n-octyloxybiphenyl-4'-carboxylic acid chloride (0.73 g) in methylene chloride (10 ml). After the mixture was left to stand until it reached room temperature, it was 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 residue was purified by silica-gel column chromatography to obtain the titled compound (0.4 g, [α]D20 =+32.2).

Workup

  1. waitAfter the 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 residue was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-b7ed3afddaec4033a1e139f8d661a7f7
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Reaction notes

Loading…