Acetic Acid → Methyl trans-3-(2,4,6-trimethoxyphenyl)acrylate

HRID 547972Notes

Reaction equation

HRID 547972 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.[CH3:13][O:14][CH:15]([O:21]C)[CH2:16][C:17](OC)=O.C(O)(=O)C.Cl>O>[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:17]=[CH:16]/[C:15]([O:14][CH3:13])=[O:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 693011,3,5-TrimethoxybenzeneHCID 81924Methyl 3,3-dimethoxypropionate

Product 1

HCID 23124870Methyl trans-3-(2,4,6-trimethoxyphenyl)acrylateYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.7 g of 1,3,5-trimethoxybenzene, 1.68 g of methyl 3,3-dimethoxypropionate and 12 mL of glacial acetic acid were mixed, 313 mg of 35 wt % hydrochloric acid was added into the mixture at an inner temperature of 25° C., the added mixture was stirred for 1 hour 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 2.46 g of methyl trans-3-(2,4,6-trimethoxyphenyl)acrylate (white solid). Yield: 98%.

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-874a3fc238b54f728810401f09eaa3ad
Source dataset
uspto-grants-2011_05
Patent number
US07939674B2

Reaction notes

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