Sodium Methoxide → HCID 21245515, compound

HRID 620943Notes

Reaction equation

HRID 620943 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:2][CH2:3][CH3:4].[CH3:17][O-:18].[Na+]>C(OC)=O>[CH:17]([CH:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[O:5][CH2:1][CH2:2][CH2:3][CH3:4])[C:13]([O:15][CH3:16])=[O:14])=[O:18]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 21245517HCID 21245517, compound

Product 1

HCID 21245515HCID 21245515, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 7865Methyl formateSolvent

Procedure

11.1 g of the product obtained by Method D are dissolved in 50 ml of methyl formate, and the solution is slowly added at 0° C. to 3.5 g of sodium methylate. The mixture is warmed to room temperature, and the bulk of the methyl formate is removed under reduced pressure. The remainder is poured onto cold 2N NaOH, and the mixture is extracted with 30 ml of methyl t-butyl ether. The aqueous phase is acidified, and the methyl α-formyl(2-butoxyphenyl)acetate is extracted with dichloromethane. Drying the organic phase over Na2SO4 gives 10.2 g (82%) of pure product.

Workup

  1. customthe bulk of the methyl formate is removed under reduced pressure
  2. additionThe remainder is poured onto cold 2N NaOH
  3. extractionthe mixture is extracted with 30 ml of methyl t-butyl ether
  4. extractionthe methyl α-formyl(2-butoxyphenyl)acetate is extracted with dichloromethane
  5. dry with materialDrying the organic phase over Na2SO4

Sources & evidence

ORD record
ord-2ef06a1c037047ebbb2545f27367a3a4
Source dataset
uspto-grants-1989_04
Patent number
US04822908

Reaction notes

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