Sodium Sulfite → 4-[2-Ethoxy-2-(2,2,2-trichloro-ethoxy carbonyl)-ethyl]-benzoic acid

HRID 1628159노트

반응식

HRID 1628159 반응식
[Cl:1][C:2]([Cl:21])([Cl:20])[CH2:3][O:4][C:5](=[O:19])[CH:6]([O:16][CH2:17][CH3:18])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1.[O-:22][Mn](=O)(=O)=O.[K+].[O-]S([O-])=O.[Na+].[Na+]>CC(C)=O.CCOC(C)=O.Cl>[CH2:17]([O:16][CH:6]([C:5]([O:4][CH2:3][C:2]([Cl:20])([Cl:21])[Cl:1])=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:22])=[O:15])=[CH:10][CH:9]=1)[CH3:18]

참가 물질

7

반응물 3

HCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 668648052-Ethoxy-3-(4-hydroxymethyl-phenyl)-propionic acid 2,2,2-trichloroethyl ester

생성물 1

HCID 668653064-[2-Ethoxy-2-(2,2,2-trichloro-ethoxy carbonyl)-ethyl]-benzoic acid

시약·촉매·용매 3

HCID 180Acetone용매HCID 313Hydrochloric Acid용매HCID 8857Ethyl Acetate용매

실험 절차

2-Ethoxy-3-(4-hydroxymethyl-phenyl)-propionic acid 2,2,2-trichloroethyl ester (0.044 g, 0.125 mmol) was dissolved in acetone (3 mL) and KMnO4 (0.039 g, 0.247 mmol) was added and the purple solution was stirred for 4 h at room temperature. Saturated aq. Na2SO3 solution was added and after 2 min. stirring, the mixture was diluted with EtOAc and aq. HCl (2N) resulting in two clear and colorless phases. The organic layer was separated and dried (MgSO4) and evaporated to afford the desired carboxylic acid which was proceeded on to the next step without further purification (0.034 g, 75%). 1H NMR (400 MHz, CDCl3): δ 8.01-8.03 (d, 2H), 7.36-7.38 (d, 2H), 4.73-4.83 (q, 2H), 4.15-4.18 (m, 1H), 3.65-3.69 (m, 1H), 3.33-3.37 (m, 1H), 3-07-3.20 (m, 2H), 1.14 (t, 3H).

후처리

  1. stirringstirring
  2. customresulting in two clear
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-ff1300579fd746a8a249cc1c75a5cc36
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785681B2

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