1,2,3-Trimethoxybenzene → 5-Oxo-5-(2,3,4-trimethoxy-phenyl)-pentanoic acid methyl ester

HRID 1944640Notes

Reaction equation

HRID 1944640 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].[CH3:13][O:14][C:15](=[O:22])[CH2:16][CH2:17][CH2:18][C:19]([O-])=[O:20]>>[CH3:13][O:14][C:15](=[O:22])[CH2:16][CH2:17][CH2:18][C:19](=[O:20])[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 69931945-Methoxy-5-oxopentanoate

Product 1

HCID 689200075-Oxo-5-(2,3,4-trimethoxy-phenyl)-pentanoic acid methyl esterYield 77%

Conditions

Temperature
45 °C

Procedure

75 g of polyphosphoric acid (Acros) was charged in a 250 mL round bottom flask, followed by addition of 1,2,3-trimethoxybenzene (5.0 g, 29.73 mmol), and mono-methylglutarate (6.516 g, 44.60 mmol). The reaction mixture was stirred mechanically for 2.5 h at 45° C. The reaction mixture was then poured into a 1000 mL beaker containing around 250 mL of ice, and stirred well until all the product precipitated out. The tan colored product was then filtered and washed with water and dried under vacuum. No, purification required at this stage. 6.78 g (77%) of product 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. customprecipitated out
  4. filtrationThe tan colored product was then filtered
  5. washwashed with water
  6. customdried under vacuum
  7. customNo, purification

Sources & evidence

ORD record
ord-e4cce71e06af4d6790703f38b7c934cd
Source dataset
uspto-grants-2013_03
Patent number
US08394859B2

Reaction notes

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