Sodium Methoxide → HCID 136091919, compound

HRID 450848Notes

Reaction equation

HRID 450848 reaction equation
C[O-].[Na+].[CH3:4][O:5][C:6]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:7]=1[C:8]([CH2:10][O:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([O:16]C)=O)=[O:9]>CO>[CH3:4][O:5][C:6]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:7]=1[C:8]([C:10]1[O:11][C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]=1[OH:16])=[O:9]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58707358HCID 58707358, compound

Product 1

HCID 136091919HCID 136091919, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of sodium methoxide (0.04 g, 0.67 mmol) in methanol was added to a solution of methyl 2-(2,5-dimethoxybenzoylmethoxy)-benzoate (0.20 g, 0.60 mmol) in dry methanol (20 ml) at 0° C. The reaction mixture was stirred at room temperature for 5 h. The reaction mixture was concentrated under reduced pressure and water was added, then extracted with ethyl acetate (three timer 30 ml). The organic layer was wahed with water, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography eluting with a gradient from 12% to 20% ethyl acetate in hexane to get the title product, m.p. 158° C. 1H-NMR (CDCl3, 400 MHz): 3.81 (s 3H), 3.83 (s, 3H), 6.99 (d, 1H), 7.07 (dd, 1H), 7.19 (d, 1H), 7.28 (d, 1H) 7.37 (d, 1H), 7.50 (t, 1H), 7.80 (d 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added
  3. extractionextracted with ethyl acetate (three timer 30 ml)
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a gradient from 12% to 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c41c5a9b4daf4082a6f875f9d1cd76f7
Source dataset
uspto-grants-2013_07
Patent number
US08486996B2

Reaction notes

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