Potassium Carbonate → HCID 19857235, compound

HRID 2073535Notes

Reaction equation

HRID 2073535 reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9]Cl)([O:3][CH3:4])=[O:2].[C:15]([CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:30]=[C:29]([OH:31])[CH:28]=[CH:27][C:24]=1[CH:25]=[O:26])([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:15]([CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:30]=[C:29]([O:31][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[O:6][CH2:5][C:1]([O:3][CH3:4])=[O:2])[CH:28]=[CH:27][C:24]=1[CH:25]=[O:26])([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13824491HCID 13824491, compoundHCID 19857249HCID 19857249, compound

Product 1

HCID 19857235HCID 19857235, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-carbomethoxymethoxybenzyl chloride (0.1 mol) and 3-carbomethoxypropoxy-4-hydroxybenzaldehyde (0.08 mol) in 8:1-acetone: dimethylformamide (900 mL) is refluxed with anhydrous potassium carbonate (0.1 mol). When the reaction is complete, the cooled reaction mixture is filtered and evaporated. The resulting oil is diluted with ethyl acetate and washed with water (6X's). The dried ethyl acetate solution is absorbed on silica gel and eluted through a column of flash silica (500 g) with a mixture of ethyl acetate: petroleum ether. Condensation of the appropriate fraction gives 3-carbomethoxypropoxy-4-(2-(carbomethoxymethoxy)phenyl)methyloxybenzaldehyde which is used directly in the next step.

Workup

  1. customthe cooled reaction mixture
  2. filtrationis filtered
  3. customevaporated
  4. additionThe resulting oil is diluted with ethyl acetate
  5. washwashed with water (6X's)
  6. customThe dried ethyl acetate solution is absorbed on silica gel
  7. washeluted through a column of flash silica (500 g) with a mixture of ethyl acetate
  8. customCondensation of the appropriate fraction

Sources & evidence

ORD record
ord-b26e29f630694b7d8d34ab1244a55786
Source dataset
uspto-grants-1990_04
Patent number
US04918081

Reaction notes

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