Benzoate → 3-Fluoro-4-(1,1,1-trifluoro-2-octyloxycarbonyl)phenyl 4-octyloxybiphenyl-4'-carboxylate

HRID 247791Notes

Reaction equation

HRID 247791 reaction equation
C([O-])(=O)C1C=CC=CC=1.[F:10][C:11]1[CH:30]=[C:29]([OH:31])[CH:28]=[CH:27][C:12]=1[C:13]([O:15][CH:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:17]([F:20])([F:19])[F:18])=[O:14].CN(C1C=CC=CN=1)C.[CH2:41]([O:49][C:50]1[CH:55]=[CH:54][C:53]([C:56]2[CH:61]=[CH:60][C:59]([C:62](Cl)=[O:63])=[CH:58][CH:57]=2)=[CH:52][CH:51]=1)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>C(Cl)Cl.O.C(N(CC)CC)C>[CH2:41]([O:49][C:50]1[CH:55]=[CH:54][C:53]([C:56]2[CH:61]=[CH:60][C:59]([C:62]([O:31][C:29]3[CH:28]=[CH:27][C:12]([C:13]([O:15][CH:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:17]([F:19])([F:20])[F:18])=[O:14])=[C:11]([F:10])[CH:30]=3)=[O:63])=[CH:58][CH:57]=2)=[CH:52][CH:51]=1)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]

Participants

8

Reactant 4

HCID 242BenzoateHCID 218852-DimethylaminopyridineHCID 110784734-(4-Octyloxyphenyl)benzoyl chlorideHCID 199208191,1,1-Trifluorooctan-2-YL 2-fluoro-4-hydroxybenzoate

Product 1

HCID 537499373-Fluoro-4-(1,1,1-trifluoro-2-octyloxycarbonyl)phenyl 4-octyloxybiphenyl-4'-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of the benzoate (1.6 g) obtained in (1) above, triethylamine (0.5 g) and dimethylaminopyridine (0.5 g) in methylene chloride (10 ml) was slowly added under cooling a solution of 4-n-octyloxybiphenyl-4'-carboxylic acid chloride (1.7 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 residue was purified by silica-gel column chromatography and recrystallized from anhydrous ethanol to obtain the titled compound (0.8 g, [α]D20 =+25.6° ). ##STR62##

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 residue was purified by silica-gel column chromatography
  8. customrecrystallized from anhydrous ethanol

Sources & evidence

ORD record
ord-d22aeb42d0fd4dbdbda7bc053208dce5
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Reaction notes

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