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

HRID 1601426Notes

Reaction equation

HRID 1601426 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-a57078cefae746659648d67929ca7826
Source dataset
uspto-grants-1999_11
Patent number
US05977139

Reaction notes

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