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

HRID 709474Notes

Reaction equation

HRID 709474 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-87f1dc6b7baf42a4bcfaaba52e8fcb00
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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