1,2-Dichloroethane → 4-(2-Chloro-ethoxy)-benzoic acid methyl ester

HRID 2289155Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Li+].[Li+].CS(C)=O.[Cl:22][CH2:23][CH2:24]Cl>>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:24][CH2:23][Cl:22])=[CH:6][CH:5]=1

Participants

Reactant 4

HCID 111,2-Dichloroethane

HCID 679Dimethyl Sulfoxide

HCID 7456Methylparaben

HCID 11125Lithium Carbonate

Product 1

HCID 64854314-(2-Chloro-ethoxy)-benzoic acid methyl ester

Procedure

4-hydroxybenzoic acid methyl ester (1.52 g, 10 mmol), anhydrous lithium carbonate (740 mg, 10 mmol), 15 ml of dimethylsulfoxide, and 15 ml of 1,2-dichloroethane are combined and heated to reflux. HPLC shows the reaction is at equilibrium at about 2 hours with a product to starting material ratio of 22.7:68.7.

Workup

temperatureheated to reflux

Sources & evidence

ORD record: ord-0378a2205f3945afaacfa11c920c8fbf
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06090949

Reaction notes

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