Dimethylformamide → HCID 12397048, compound

HRID 2254468Notes

Reaction equation

HRID 2254468 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[H-].[Na+].CN(C)C=O.[CH3:18][O:19][CH2:20]Cl>O1CCCC1>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:18][O:19][CH3:20])[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 87683,4-DihydroxybenzaldehydeHCID 24758Sodium hydride

Product 1

HCID 12397048HCID 12397048, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3 g of 3,4-dihydroxybenzaldehyde and 0.87 g of 60% oily sodium hydride were suspended in 13 ml of tetrahydrofuran, and a dimethylformamide solution (10 ml) of 3.3 ml of methoxymethyl chloride was added. The mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was distributed between ethyl acetate and water, the organic layer was worked up in a customary manner, and then purified by silica gel column chromatography [Wakogel C-200, 150 g; eluting solvent: hexane/ethyl acetate=4/1] to give 1.78 g (yield 45%) of 3-hydroxy-4-methoxymethyloxybenzaldehyde.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by silica gel column chromatography [Wakogel C-200, 150 g; eluting solvent: hexane/ethyl acetate=4/1]

Sources & evidence

ORD record
ord-0d8e28e01b804b409806581c89e82c61
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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