HCID 24965836, compound → HCID 59054016, compound

HRID 1751913Notes

Reaction equation

HRID 1751913 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)=[CH:8][CH:7]=1)[OH:5]>ClCCl.[O-2].[Mn+4].[O-2]>[CH3:1][O:2][C:3](=[O:22])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)=[CH:10][CH:11]=1)=[O:5]

Participants

4

Reactant 1

HCID 24965836HCID 24965836, compound

Product 1

HCID 59054016HCID 59054016, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

[4-(3,4-Dichlorobenzyloxy)phenyl]-hydroxy-acetic acid methyl ester (85.25 g) was dissolved in dry dichloromethane (500 mL). To the resulting solution, activated manganese (IV) oxide (<5 μm, 175 g) was added. The mixture was stirred vigorously for about 12 hours (until TLC showed no presence of unreacted starting material). The reaction mixture (slurry) was diluted with dichloromethane (500 mL) and was passed through a pad of celite. The filtrate was concentrated to yield the title compound. Proton NMR (400 MHz, CDCl3) was recorded. The following chemical shifts (in ppm) were recorded relative to TMS reference of 0.0 ppm, and include the following: 3.97 (s, 3H); 5.11 (s, 2H); 7.03 (m, 2H); 7.26 (m, 1H); 7.47 (d, 1H); 7.54 (d, 1H); 8.02 (m, 2H).

Workup

  1. additionwas added
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9fa6a705b1ef4acaaebbef29477226e0
Source dataset
uspto-grants-2015_10
Patent number
US09162963B2

Reaction notes

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