3,4,5-Trimethoxybenzoic Acid → HCID 19866343, compound

HRID 1199309Notes

Reaction equation

HRID 1199309 reaction equation
S(Cl)([O:4][CH2:5][Cl:6])(=O)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20])[C:13](O)=[O:14].C(=O)([O-])O.[Na+]>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[CH3:22][O:21][C:17]1[CH:16]=[C:12]([CH:11]=[C:10]([O:9][CH3:8])[C:18]=1[O:19][CH3:20])[C:13]([O:4][CH2:5][Cl:6])=[O:14]

Participants

7

Reactant 3

HCID 83573,4,5-Trimethoxybenzoic AcidHCID 516892Sodium BicarbonateHCID 2733556Chloromethyl chlorosulfate

Product 1

HCID 19866343HCID 19866343, compoundYield 40.5%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolventHCID 21908982Water methylene chlorideSolvent

Procedure

19 g of chloromethyl chlorosulphate in 30 ml of methylene chloride are introduced dropwise at room temperature into a stirred mixture of 21.1 g of 3,4,5-trimethoxybenzoic acid, 33.6 g of sodium hydrogen carbonate and 3.4 g of tetrabutylammonium hydrogen sulphate in 600 ml of methylene chloride-water (1:1). In order to complete the reaction, the mixture is stirred at room temperature for a further 2 hours, the two phases are then separated, the aqueous phase is washed with 100 ml of methylene chloride and the combined organic phases are dried over sodium sulphate. The solvent is removed in a vacuum and the residue is chromatographed over 450 g of silica gel with methylene chloride. Fractions containing the product are evaporated and the residue is crystallized from methylene chloride-petroleum ether. 10.5 g of chloromethyl 3,4,5-trimethoxybenzoate are obtained as colourless needles with a melting point of 85°-86°. RF (silica gel/methylene chloride): 0.45.

Workup

  1. customthe reaction
  2. customthe two phases are then separated
  3. washthe aqueous phase is washed with 100 ml of methylene chloride
  4. dry with materialthe combined organic phases are dried over sodium sulphate
  5. customThe solvent is removed in a vacuum
  6. customthe residue is chromatographed over 450 g of silica gel with methylene chloride
  7. additionFractions containing the product
  8. customare evaporated
  9. customthe residue is crystallized from methylene chloride-petroleum ether

Sources & evidence

ORD record
ord-7947663cc4ef45678e2666102701a2da
Source dataset
uspto-grants-1990_02
Patent number
US04900478

Reaction notes

Loading…