Benzyl Alcohol → Pentafluorobenzoic acid, benzyl ester

HRID 729360

반응식

HRID 729360 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 517856Pentafluorobenzoic acid, benzyl ester수율 77.3%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bf56666aa0ca4581ad3c2f56c7c7d28f
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582627B2

연결된 노트

불러오는 중…