1,2,3-Trimethoxybenzene → 4-Oxo-4-(2,3,4-trimethoxy-phenyl)-butyric acid methyl ester

HRID 33958Notes

Reaction equation

HRID 33958 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].[C:13]([O:20][CH3:21])(=[O:19])[CH2:14][CH2:15][C:16]([O-])=[O:17]>>[CH3:21][O:20][C:13](=[O:19])[CH2:14][CH2:15][C:16](=[O:17])[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([O:11][CH3:12])[C:5]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 124621,2,3-TrimethoxybenzeneHCID 6930703Mono-Methyl Succinate

Product 1

HCID 447204584-Oxo-4-(2,3,4-trimethoxy-phenyl)-butyric acid methyl esterYield 72.7%

Conditions

Temperature
45 °C

Procedure

A mixture of 75 g of polyphosphoric acid (Acros), 1,2,3-trimethoxybenzene (5.0 g, 29.73 mmol), and mono-methyl succinate (5.9 g, 44.59 mmol) were mechanically stirred at 45° C. for 2.5 h. The reaction mixture was then poured into a 1000 mL beaker containing round 250 mL of ice, and stirred well until all the product was precipitated out. The tan colored product was then filtered and washed with water and dried under vacuum. 6.1 g (72%) of 55 was obtained, which was pure by NMR.

Workup

  1. additionThe reaction mixture was then poured into a 1000 mL beaker
  2. stirringstirred well until all the product
  3. customwas precipitated out
  4. filtrationThe tan colored product was then filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-bdb5c2efb4434099bfacdae154ddb13a
Source dataset
uspto-grants-2008_09
Patent number
US07429681B2

Reaction notes

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