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

HRID 1095920ノート

反応式

HRID 1095920 の反応式
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]

参加物

8

反応物 4

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

生成物 1

HCID 573835072-Chloro-4-methoxyphenylacetic acid methylester収率 88%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

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+].

後処理

  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)

出典と根拠

ORDレコード
ord-5d5b51d50f754833bf2df344614e620d
出典データセット
uspto-grants-2012_03
特許番号
US08138189B2

反応ノート

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