Phosphorus oxychloride → Methyl trans-3-(2,4,6-trimethoxyphenyl)acrylate

HRID 644101Notes

Reaction equation

HRID 644101 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[CH:4]=1.CO/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18].P(Cl)(Cl)(Cl)=O>O.C(O)(=O)C>[CH3:12][O:11][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[C:6]=1/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18]

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 693011,3,5-TrimethoxybenzeneHCID 5323651Methyl 3-methoxyacrylate

Product 1

HCID 23124870Methyl trans-3-(2,4,6-trimethoxyphenyl)acrylateYield 91%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

1.68 g of 1,3,5-trimethoxybenzene, 2.32 g of methyl trans-3-methoxyacrylate, 0.18 g of water and 6 mL of glacial acetic acid were mixed, 164 mg of phosphorus oxychloride was added into the mixture at an inner temperature of 25° C., the added mixture was stirred for 3 hours at the same temperature to cause a reaction. After completion of the reaction, 36 mL of water was added dropwise into the reaction liquid, and the precipitated crystals were filtrated. The crystals were washed with 20 vol % of aqueous methanol, then, dried to obtain 2.28 g of methyl trans-3-(2,4,6-trimethoxyphenyl)acrylate (white solid). Yield: 91%.

Workup

  1. customa reaction
  2. additionwas added dropwise into the reaction liquid
  3. filtrationthe precipitated crystals were filtrated
  4. washThe crystals were washed with 20 vol % of aqueous methanol
  5. customdried

Sources & evidence

ORD record
ord-52c7305466fd4b2294dea847e567c99c
Source dataset
uspto-grants-2010_04
Patent number
US07700642B2

Reaction notes

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