Formaldehyde → HCID 86736903, compound

HRID 615451Notes

Reaction equation

HRID 615451 reaction equation
Cl[CH:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]C)[C:3]([O:5][CH3:6])=[O:4].[CH3:21][O-:22].[Li+].[CH2:24]=O>CN(C=O)C>[CH3:24][CH:7]([C:2]1([O:22][CH2:21]1)[C:3]([O:5][CH3:6])=[O:4])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 572540Methyl 2-chlorohexadecanoateHCID 4177230Lithium methanolate

Product 1

HCID 86736903HCID 86736903, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl α-chloropalmitate (6.1 g, 0.02 m) was dissolved in 40 ml DMF and treated with lithium methoxide (0.84, 0.022 m) followed by portionwise addition of paraformaldehyde (0.63 g, 0.021 m) over a period of about eight hours. The reaction mixture was stirred at room temperature overnight. The reaction was worked up by neutralization to pH 7 with methanol-HCl, evaporation of the DMF; the residue was dissolved in ether and filtered. Evaporation of the ether led to 99.5 percent recovery of methyl 2-tetradecylglycidate as an oil. Crystallization from methanol (twice) gave material with a melting point of 40°-42°.

Workup

  1. customThe reaction was worked up by neutralization to pH 7 with methanol-HCl, evaporation of the DMF
  2. dissolutionthe residue was dissolved in ether
  3. filtrationfiltered
  4. customEvaporation of the ether
  5. customCrystallization from methanol (twice)
  6. customgave material with a melting point of 40°-42°

Sources & evidence

ORD record
ord-eca0d70f30d34b60a2ce276f5857e0ce
Source dataset
uspto-grants-1985_02
Patent number
US04499294

Reaction notes

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