Water → 3,4-Dichlorobenzyl 2-(4-((3,4-dichlorobenzyl)oxy)phenyl)-2-hydroxyacetate

HRID 39056Notes

Reaction equation

HRID 39056 reaction equation
O.[OH:2][CH:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5].C([O-])([O-])=O.[K+].[K+].[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:24]Br.O>CN(C=O)C>[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:24][O:5][C:4](=[O:6])[CH:3]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:24][C:23]2[CH:26]=[CH:27][C:28]([Cl:29])=[C:21]([Cl:20])[CH:22]=2)=[CH:9][CH:8]=1)[OH:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 126772902-Hydroxy-2-(4-hydroxyphenyl)acetic acid hydrate

Product 1

HCID 669225903,4-Dichlorobenzyl 2-(4-((3,4-dichlorobenzyl)oxy)phenyl)-2-hydroxyacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of hydroxy-(4-hydroxy-phenyl)-acetic acid monohydrate (10 g) in DMF (50 mL) was added K2CO3 (29.7 g), followed by 3,4-dichlorobenzyl bromide (16.1 mL). The mixture was stirred at room temperature for 3 h. The mixture was poured into water (250 mL) and extracted with EtOAc. The organic layer was washed with water 1N HCl, brine, dried over Na2SO4, and concentrated. The resulting solid was triturated with diethyl ether and filtered to provide [4-(3,4-dichloro-benzyloxy)-phenyl]-hydroxy-acetic acid 3,4-dichloro-benzyl ester as a white solid (9.4 g). 1H NMR (400 MHz, DMSO d6): 7.69 (d, 1H), 7.63 (d, 1H), 7.55 (d, 1H), 7.41 (m, 1H), 7.37 (d, 1H), 7.31 (m, 2H), 7.20 (m, 1H), 6.97 (m, 2H), 6.06 (d, 1H), 5.16 (d, 1H), 5.1 (m, 4H).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water 1N HCl, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting solid was triturated with diethyl ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-1e576cd405ff423d91b636f18df7e43d
Source dataset
uspto-grants-2013_09
Patent number
US08524708B2

Reaction notes

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