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

HRID 323224Notes

Reaction equation

HRID 323224 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-trimethoxybenzoic acid (3.5 kg, 16.5 mol) and 1,2-dimethoxyethane (14.2 kg) and dimethyl formamide (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-trimethoxybenzoyl 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-1d1e1b2c48634d20af76c0d87b6c25bf
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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