Formaldehyde → HCID 20194908, compound

HRID 653510Notes

Reaction equation

HRID 653510 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][CH2:5][CH:6]([C:11]([O:13][CH3:14])=[O:12])[C:7]([O:9][CH3:10])=[O:8].C=O.[C:19](=O)([O-])[OH:20].[K+]>>[OH:20][CH2:19][C:6]([C:11]([O:13][CH3:14])=[O:12])([C:7]([O:9][CH3:10])=[O:8])[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[O:15][CH3:16]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 516893Potassium BicarbonateHCID 13379916Dimethyl (3,3-dimethoxypropyl)propanedioate

Product 1

HCID 20194908HCID 20194908, compoundYield 95%

Procedure

The hydroxymethylation of dimethyl 4,4-dimethoxybutane-1,1-dicarboxylate was carried out. The diester (23.4 g, 0.10 mol) was added dropwise to a mixture of formalin (8.1 ml, 0.10 mol) and potassium hydrogen carbonate (0.8 g, 8 mmol) over 20 min. The mixture was stirred at room temperature for 6 hours until the starting ester was completely consumed. A saturated aqueous solution of ammonium sulfate (35 ml) was added to the reaction mixture. The mixture was then extracted with three 60 ml portions of ethyl ether and the combined extracts were dried over anhydrous magnesium sulfate. The salt was filtered off and rotary evaporation of the solvent from the filtrate gave the product, at 95% yield, as viscous oil.

Workup

  1. customwas completely consumed
  2. additionA saturated aqueous solution of ammonium sulfate (35 ml) was added to the reaction mixture
  3. extractionThe mixture was then extracted with three 60 ml portions of ethyl ether
  4. dry with materialthe combined extracts were dried over anhydrous magnesium sulfate
  5. filtrationThe salt was filtered off
  6. customrotary evaporation of the solvent from the filtrate
  7. customgave the product

Sources & evidence

ORD record
ord-0e7c2b7837f24f42b0132d133bab76c9
Source dataset
uspto-grants-1987_06
Patent number
US04677190

Reaction notes

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