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

HRID 21423

Reaction equation

HRID 21423 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].CN(C1C=CC=CN=1)C.C(N(CC)CC)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 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-benzyloxybenzoic acid chloride (4.3 g) in methylene chloride (50 ml) was added drop by drop a solution of (R)-(+)-1,1,1-trifluoro-2-octanol (2.9 g), dimethylaminopyridine (0.6 g) and triethylamine (1.7 g) in methylene chloride (50 ml), under ice cooling. The mixture was left to stand at the room temperature for 24 hours before being poured in ice water. The methylene chloride layer separated was washed with diluted hydrochloric acid, water 1N aqueous sodium carbonate solution and water in this order, dried over magnesium sulfate and distilled to obtain a crude objective compound. The compound was purified by toluene/silica gel chromatography and recrystallization from ethanol to obtain the titled compound (3.8 g).

Workup

  1. waitThe mixture was left
  2. customThe methylene chloride layer separated
  3. washwas washed with diluted hydrochloric acid, water 1N aqueous sodium carbonate solution and water in this order
  4. dry with materialdried over magnesium sulfate
  5. distillationdistilled
  6. customto obtain a crude objective compound
  7. customThe compound was purified by toluene/silica gel chromatography and recrystallization from ethanol

Sources & evidence

ORD record
ord-b0bbf4059f3f4f6985f90088f6ed8e04
Source dataset
uspto-grants-1995_06
Patent number
US05424005

Linked notes

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