Formaldehyde → HCID 86736903, compound

HRID 615452Notes

Reaction equation

HRID 615452 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, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl α-chloropalmitate (61 g, 0.20 m) was dissolved in 400 ml DMF and treated with lithium methoxide (8.35 g, 0.22 m) followed by portionwise addition of paraformaldehyde (6.3 g, 0.21 m) over a period of about eight hours. The reaction was stirred overnight, 12 hours after complete addition, at room temperature. It was worked up by extraction with hexane; the hexane was dried and evaporated to yield 53 g (89 percent) methyl 2-tetradecylglycidate (97 percent purity by glc) with m.p. 45°-48° C. after recrystallization from methanol.

Workup

  1. additionafter complete addition
  2. customat room temperature
  3. extractionIt was worked up by extraction with hexane
  4. dry with materialthe hexane was dried
  5. customevaporated

Sources & evidence

ORD record
ord-cfb2c43ee81a4291aae7362a1e5a8678
Source dataset
uspto-grants-1985_02
Patent number
US04499294

Reaction notes

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