Ethyl orthoformate → Ethyl 3-chloro-2-methylbenzoate

HRID 434487Notes

Reaction equation

HRID 434487 reaction equation
[CH3:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12](OC(OCC)OCC)[CH3:13]>>[CH2:12]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([Cl:11])[C:2]=1[CH3:1])[CH3:13]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 820103-Chloro-2-methylbenzoic acid

Product 1

HCID 13187238Ethyl 3-chloro-2-methylbenzoateYield 89%

Procedure

A mixture of 34 g. (0.2 mol) of 2-methyl-3-chlorobenzoic acid and 50 mL. of commercially available triethylorthoformate was refluxed for 6 hours, upon which bulb-to-bulb distillation gave 35.5 g. (89% yield) of ethyl-3-chloro-2-methylbenzoate as a clear liquid having a boiling point of 80° C. at a pressure of 0.1 mmHg.

Workup

  1. additionA mixture of 34 g
  2. customgave 35.5 g

Sources & evidence

ORD record
ord-7b884260a2644e8f9360a9559ac1834f
Source dataset
uspto-grants-1983_08
Patent number
US04397790

Reaction notes

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