Formaldehyde → Methyl 2-tetradecyloxirane-2-carboxylate

HRID 615454Notes

Reaction equation

HRID 615454 reaction equation
[H-].[Li+].[CH2:3]=[O:4].CO.Cl[CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:9]([O:11][CH3:12])=[O:10]>CN(C=O)C>[CH2:13]([C:8]1([O:4][CH2:3]1)[C:9]([O:11][CH3:12])=[O:10])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 712Formaldehyde2×HCID 887MethanolHCID 62714Lithium hydrideHCID 572540Methyl 2-chlorohexadecanoate

Product 1

HCID 68593Methyl 2-tetradecyloxirane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Lithium hydride (0.32 g, 0.040 m), paraformaldehyde (0.16 g, 0.0053 m), and methanol (0.32 g, 0.010 m) were heated together in 25 ml DMF at 30°-40° C. After 1 hour, methyl α-chloropalmitate (3.05 g, 0.010 m) was added; the remaining paraformaldehyde (0.16 g, 0.0053 m) was added in two portions. The reaction was worked up after 51/2 hours of heating. The reaction mixture was extracted with hexane; the hexane was washed with water and dried over Na2SO4. The mixture was filtered and stripped to a crystalline residue. The residue was recrystallized from methanol to give 2.49 g (83.5%) yield of methyl tetradecylglycidate (m.p. 47°-48° C., glc purity>99%).

Workup

  1. custom2 hours
  2. temperatureof heating
  3. extractionThe reaction mixture was extracted with hexane
  4. washthe hexane was washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationThe mixture was filtered
  7. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-4ddfd600cfa948eb9ed99b82d534eb3c
Source dataset
uspto-grants-1985_02
Patent number
US04499294

Reaction notes

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