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

HRID 1590014Notes

Reaction equation

HRID 1590014 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])[C@H: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 2779099(R)-(+)-1,1,1-Trifluoro-2-octanolHCID 37664104-Benzyloxybenzoylchloride

Product 1

HCID 14549213Benzoic acid, 4-(phenylmethoxy)-, 1-(trifluoromethyl)heptyl esterYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 20 ml of methylene chloride was dissolved 1.1 g of 4-benzyloxybenzoic acid chloride, and to the solution was slowly added a solution of 0.74 g of (R)-(+)-1,1,1-trifluoro-2-octanol ([α]D20 =+25.2°), 0 4 g of triethylamine, and a catalytic amount of dimethylaminopyridine in 10 ml of methylene chloride under ice-cooling. After warming to room temperature, the solution was stirred for 12 hours. The reaction mixture was poured into ice-water and extracted with methylene chloride. The methylene chloride phase was successively washed with diluted hydrochloric acid, water, an aqueous 1N sodium carbonate solution, and water and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residual crude product was purified by silica gel column chromatography to obtain 1.0 g of 1,1,1-trifluoro-2-octyl 4-benzyloxybenzoate.

Workup

  1. extractionextracted with methylene chloride
  2. washThe methylene chloride phase was successively washed with diluted hydrochloric acid, water
  3. dry with materialan aqueous 1N sodium carbonate solution, and water and then dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe residual crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-22895893583640bfabf2294645029065
Source dataset
uspto-grants-1993_04
Patent number
US05202054

Reaction notes

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