Acetic Acid → Methyl (2E)-3-(2,3,4-trimethoxyphenyl)-2-propenoate

HRID 644103Notes

Reaction equation

HRID 644103 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[O:11][CH3:12].CO/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18].C(O)(=O)C.Cl>C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[C:4]([O:11][CH3:12])=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][C:8]=1/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 124621,2,3-TrimethoxybenzeneHCID 5323651Methyl 3-methoxyacrylate

Product 1

HCID 11043219Methyl (2E)-3-(2,3,4-trimethoxyphenyl)-2-propenoateYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.68 g of 1,2,3-trimethoxybenzene, 1.34 g of methyl trans-3-methoxyacrylate and 6 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 16 hours at the same temperature to cause a reaction. After completion of the reaction, 30 mL of water and 50 mL of ethyl acetate were added into the reaction liquid, and extraction treatment was conducted. The resultant organic layer was washed with water, then, concentrated, and the resultant concentrated residue was purified by silica gel column chromatography (developing liquid: n-heptane/ethyl acetate=6/1 to 5/1), to obtain 0.63 g of methyl trans-3-(2,3,4-trimethoxyphenyl)acrylate (white solid). 0.92 g of the raw material 1,2,3-trimethoxybenzene was recovered. The yield of methyl 3-(2,3,4-trimethoxyphenyl)acrylate based on the converted 1,2,3-trimethoxybenzene was 55%.

Workup

  1. customa reaction
  2. additionwere added into the reaction liquid, and extraction treatment
  3. washThe resultant organic layer was washed with water
  4. concentrationconcentrated
  5. customthe resultant concentrated residue was purified by silica gel column chromatography (developing liquid: n-heptane/ethyl acetate=6/1 to 5/1)

Sources & evidence

ORD record
ord-8db6443eea9d464689f95af6966119fe
Source dataset
uspto-grants-2010_04
Patent number
US07700642B2

Reaction notes

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