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

HRID 1628159ノート

反応式

HRID 1628159 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 313Hydrochloric Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-ff1300579fd746a8a249cc1c75a5cc36
出典データセット
uspto-grants-2014_07
特許番号
US08785681B2

反応ノート

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