Benzyl Alcohol → Pentafluorobenzoic acid, benzyl ester

HRID 10271

Reaction equation

HRID 10271 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]([F:14])[C:3]=1[C:4]([OH:6])=[O:5].[CH2:15](O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl.[Cl-].[Na+].O>[CH2:15]([O:5][C:4](=[O:6])[C:3]1[C:2]([F:1])=[C:10]([F:11])[C:9]([F:12])=[C:8]([F:13])[C:7]=1[F:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 244Benzyl AlcoholHCID 11770Pentafluorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 517856Pentafluorobenzoic acid, benzyl esterYield 77.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,3,4,5,6-pentafluorobenzoic acid (15.25 g, 71.9 mmol), 4-dimethylaminopyridine (4.4 g, 36.0 mmol) and benzyl alcohol (7.4 mL, 71.5 mmol) in dichloromethane (150 mL) is cooled to 0° C. under an inert atmosphere. 1-[3-(Dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (16.7 g, 87.1 mmol) is added and the mixture stirred at 0° C. for 2 hours. The mixture is warmed to ambient temperature, stirred for 24 hours, and then poured into brine. The mixture is extracted with chloroform and the organic phase washed with NaHCO3, dried over Na2SO4, filtered and concentrated under vacuum to yield the title compound as a white solid (16.7 g). This material is used without further purification. 1H NMR (CDCl3): δ 7.49–7.27 (m, 5H), 5.40 (s, 2H).

Workup

  1. temperatureThe mixture is warmed to ambient temperature
  2. stirringstirred for 24 hours
  3. extractionThe mixture is extracted with chloroform
  4. washthe organic phase washed with NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0840a894e93d4828b9a71ddc2cef0484
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Linked notes

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