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

HRID 2226069Notes

Reaction equation

HRID 2226069 reaction equation
[F:1][C:2]([F:12])([F:11])[C@H:3]([OH:10])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH2:13]([O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN(C1C=CC=CN=1)C.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl.O.C(N(CC)CC)C>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:10][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[C:2]([F:11])([F:12])[F:1])=[O:26])=[CH:28][CH:29]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 218852-DimethylaminopyridineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2779099(R)-(+)-1,1,1-Trifluoro-2-octanolHCID 37664104-Benzyloxybenzoylchloride

Product 1

HCID 14549213Benzoic acid, 4-(phenylmethoxy)-, 1-(trifluoromethyl)heptyl esterYield 50.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

After 3.7 g of (R)-(+)-1,1,1-trifluoro-2-octanol and 1.2 g of triethylamine were added to 40 ml of methylene chloride to form a mixture, 40 ml of methylene chloride solution containing 4.3 g of 4-benzyloxybenzoic acid chloride was dropped with stirring to the mixture. Further, 0.5 g of dimethylaminopyridine was added and the mixture thus formed was stirred at an ambient temperature for a whole day and night. Thereafter, the reaction liquid was poured in a water tank to make it neutral. After the methylene chloride layer thus formed was extracted, the reaction liquid was dehydrated with an anhydrous magnesium sulfate. After the solvent was distilled off, the reaction product thus formed was subjected to separation and purification by a silica gel column chromatography to obtain 3.5 g of the objective compound.

Workup

  1. additionwas dropped
  2. customthe mixture thus formed
  3. stirringwas stirred at an ambient temperature for a whole day and night
  4. customThereafter, the reaction liquid
  5. extractionwas extracted
  6. customthe reaction liquid
  7. distillationAfter the solvent was distilled off
  8. customthe reaction product thus formed
  9. customwas subjected to separation and purification by a silica gel column chromatography

Sources & evidence

ORD record
ord-719be5242efd4b3da7f8263d98b6cc3f
Source dataset
uspto-grants-1994_09
Patent number
US05346648

Reaction notes

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