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

HRID 13569

Reaktionsgleichung

Reaktionsgleichung von HRID 13569
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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1571ba16a1714b5dbf296fcb262cea8c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727983B2

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