1,2-Dimethoxyethane → Benzoyl chloride, 3,4,5-trimethoxy-

HRID 400060Notes

Reaction equation

HRID 400060 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](O)=[O:7].COCCOC.C(Cl)(=O)C([Cl:25])=O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([Cl:25])=[O:7]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 83573,4,5-Trimethoxybenzoic AcidHCID 65578Oxalyl chloride

Product 1

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 3,4,5-trimethoxy-benzoic acid (3.5 kg, 16.5 mol) and 1,2-dimethoxyethane (14.2 kg) and dimethylformamide (4 g). Cool in an ice bath. Add oxalyl chloride (2.99 kg, 23.5 mmol) over about 50 minutes not allowing the temperature of the reaction to raise above about 19° C. After 20 hours, concentrate in vacuo at 25° C. to remove about 3.7 kg of distillate to give a solution of 3,4,5-trimethoxy-benzoyl chloride.

Workup

  1. temperatureCool in an ice bath
  2. customthe temperature of the reaction
  3. temperatureto raise above about 19° C
  4. concentrationconcentrate in vacuo at 25° C.
  5. customto remove about 3.7 kg of distillate

Sources & evidence

ORD record
ord-38224d51d299487ea53036685b1b7d6a
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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