Formic Acid → 5-(3,4-Dimethoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1256885Notes

Reaction equation

HRID 1256885 reaction equation
C(O)=O.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:9]=O.[CH3:16][C:17]1([CH3:25])[O:24][C:22](=[O:23])[CH2:21][C:19](=[O:20])[O:18]1.Cl>C(N(CC)CC)C>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH2:9][CH:21]1[C:22](=[O:23])[O:24][C:17]([CH3:25])([CH3:16])[O:18][C:19]1=[O:20]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 8419VeratraldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 103346195-(3,4-Dimethoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 88.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Under ice-cooling, to formic acid (20 mL) was added dropwise triethylamine (29.6 mL). Then, 3,4-dimethoxybenzaldehyde (9.22 g) and Meldrum's acid (8.00 g) were added under ice-cooling, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was poured into a mixture of ice (80 g) and 1 mol/L hydrochloric acid (50 mL), and the precipitate was collected by filtration to give the title compound (14.4 g) as a white solid.

Workup

  1. temperaturecooling
  2. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4608d0cff1a846a78a15f6a17062878f
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

Loading…