Formaldehyde → HCID 86736903, compound

HRID 615453Notes

Reaction equation

HRID 615453 reaction equation
[CH3:1][O-:2].[Li+].Cl[CH:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]C)[C:6]([O:8][CH3:9])=[O:7].[CH2:24]=O>CS(C)=O>[CH3:24][CH:10]([C:5]1([O:2][CH2:1]1)[C:6]([O:8][CH3:9])=[O:7])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 572540Methyl 2-chlorohexadecanoateHCID 4177230Lithium methanolate

Product 1

HCID 86736903HCID 86736903, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
35 °C

Procedure

A suspension of lithium methoxide (0.41 g, 0.011 m) in 10 ml of dry DMSO was treated with a suspension of methyl α-chloropalmitate (3.05 g, 0.010 m) in 10 ml of dry DMSO at 35° C., then with paraformaldehyde (0.300 g, 0.01 m) added portionwise over 81/2 hours. The reaction mixture was stirred at 35° C. for an additional two hours then overnight at room temperature. It was extracted with hexane. Water was added to the DMSO layer and this was extracted twice with hexane. The combined hexane extracts were washed with water, dried and evaporated to a clear oil which crystallized (2.49 g, 84%). Glc analysis of product showed 97.5 percent methyl 2-tetradecylglycidate.

Workup

  1. customovernight
  2. customat room temperature
  3. extractionIt was extracted with hexane
  4. additionWater was added to the DMSO layer
  5. extractionthis was extracted twice with hexane
  6. washThe combined hexane extracts were washed with water
  7. customdried
  8. customevaporated to a clear oil which
  9. customcrystallized (2.49 g, 84%)

Sources & evidence

ORD record
ord-b3358a7012004791b01a53e0df4208c5
Source dataset
uspto-grants-1985_02
Patent number
US04499294

Reaction notes

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