Triethylamine → Benzoic acid, 4-(phenylmethoxy)-, 1-(trifluoromethyl)heptyl ester

HRID 1195093Notes

Reaction equation

HRID 1195093 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]([F:29])([F:28])[CH:20]([OH:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:27][CH:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:19]([F:18])([F:28])[F:29])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 978042-Octanol, 1,1,1-trifluoro-HCID 37664104-Benzyloxybenzoylchloride

Product 1

HCID 14549213Benzoic acid, 4-(phenylmethoxy)-, 1-(trifluoromethyl)heptyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 20 ml of methylene chloride was dissolved 1.0 g of 4-benzyloxybenzoic acid chloride, and a solution of 0.67 g of optically active 1,1,1-trifluoro-2-octanol, 0.36 g of triethylamine, and a catalytic amount of dimethylaminopyridine in 10 ml of methylene chloride was slowly added thereto under ice-cooling. The reaction mixture was allowed to warm to room temperature, stirred at that temperature for 12 hours, poured into ice-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 dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by column chromatography using silica gel to obtain 0.65 g of 1,1,1-trifluoro-2-octyl 4-benzyloxybenzoate.

Workup

  1. temperatureunder ice-cooling
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride phase was washed successively with diluted hydrochloric acid, water
  4. dry with materialan aqueous 1N sodium carbonate solution, and water and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customto obtain a crude product
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-f58795dd901f46789acb3272e7450d27
Source dataset
uspto-grants-1992_05
Patent number
US05110498

Reaction notes

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