Water → 4-(4-Pentenyloxy)biphenyl-4'-carbox-ylic acid 4-(1,1,1-trifluoro-2-octyloxycarbonyl)-phenyl ester

HRID 1195095Notes

Reaction equation

HRID 1195095 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([CH2:27][CH3:28])CC)C.CN([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34]N=1)C.[CH2:38]([O:43][C:44]1[CH:45]=[C:46](C(Cl)=O)[C:47](C2C=CC=CC=2)=[CH:48][CH:49]=1)[CH2:39][CH2:40][CH:41]=[CH2:42].[OH2:59]>C(Cl)Cl>[F:13][C:10]([F:11])([F:12])[CH:9]([O:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][C:34]([C:35]2[CH:28]=[CH:27][C:32]([C:47]3[CH:48]=[CH:49][C:44]([O:43][CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])=[CH:45][CH:46]=3)=[CH:37][CH:36]=2)=[O:59])=[CH:21][CH:20]=1)=[O:7])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 145492151,1,1-Trifluoro-2-octyl 4-hydroxybenzoateHCID 545729574-(4-Pentenyloxy) biphenylcarboxylic acid chloride

Product 1

HCID 536482514-(4-Pentenyloxy)biphenyl-4'-carbox-ylic acid 4-(1,1,1-trifluoro-2-octyloxycarbonyl)-phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 10 ml of methylene chloride were added 0.48 g of 1,1,1-trifluoro-2-octyl 4-hydroxybenzoate, 0.16 g of triethylamine, and a catalytic amount of dimethylaminopyridine, and a solution of 0.57 g of 4-(4-pentenyloxy) biphenylcarboxylic acid chloride in 10 ml of methylene chloride was added slowly thereto under ice-cooling. The reaction mixture was allowed to warm to room temperature, followed by stirring for one day. The reaction mixture was poured into water and extracted with methylene chloride. The methylene chloride phase was washed successively with diluted hydrochloric acid, water, an aqueous 1N sodium carbonate solution, and water and dehydrated over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the crude product was purified by column chromatography using silica gel to obtain 0.33 g of the titled compound ([α]D20 =+34.3°). The resulting compound exhibited liquid crystal characteristics. The phase transition temperatures of the liquid crystal compound obtained were measured by polarizing microscopic observation using temperature controlled hot stage in which a liquid crystal cell was placed. Phase Transition Temperatures (° C.): ##STR9##

Workup

  1. temperatureunder ice-cooling
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride phase was washed successively with diluted hydrochloric acid, water
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-38677198b847430f8bdef7f182994448
Source dataset
uspto-grants-1992_05
Patent number
US05110498

Reaction notes

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