1,2-Dichloroethane → 2-Chloro-4-methoxyphenylacetic acid methylester

HRID 1095920노트

반응식

HRID 1095920 반응식
CO.[CH2:3](Cl)CCl.[Cl:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]([OH:19])=[O:18].Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(N(CC)CC)C>[CH3:3][O:18][C:17](=[O:19])[CH2:16][C:9]1[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=1[Cl:7]

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 887MethanolHCID 42091322-(2-Chloro-4-methoxyphenyl)acetic acid

생성물 1

HCID 573835072-Chloro-4-methoxyphenylacetic acid methylester수율 88%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

Methanol (12.13 mL), DMAP (609 mg), EDC (19.11 g), and triethylamine (13.88 mL) were added under cooling (ice) to a solution of (2-chloro-4-methoxy-phenyl)-acetic acid (20.00 g, [CAS Reg. No. 91367-09-8]) in CH2Cl2 (400 mL). The reaction mixture was stirred overnight at r.t. The reaction mixture was poured into ice/water and acidified with 1M aqueous HCl to pH 2. The aqueous layer was extracted two times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a colorless oil (18.77 g, 88%). MS (m/e)=215.1 [MH+].

후처리

  1. extractionThe aqueous layer was extracted two times with CH2Cl2
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

출처 및 근거

ORD 기록
ord-5d5b51d50f754833bf2df344614e620d
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138189B2

반응 노트

불러오는 중…