Formaldehyde → HCID 69158355, compound

HRID 1624296Notes

Reaction equation

HRID 1624296 reaction equation
[CH2:1]=[O:2].OS(O)(=O)=O.C([N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])C=C.[OH2:22]>>[O:2]1[CH2:19][CH2:20][CH:13]([CH2:12][C:20]2[CH:19]=[CH:18][CH:17]=[C:14]3[C:15]([NH:11][C:12](=[O:21])[C:13]=23)=[O:16])[O:22][CH2:1]1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 1118Sulfuric AcidHCID 224401N-Allylphthalimide

Product 1

HCID 69158355HCID 69158355, compoundYield 54%

Procedure

A solution of paraformaldehyde (245 g) was heated to 70° C. in a solution of H2SO4 (360 mL) and H2O (90 mL) using a hot water bath until the mixture became homogenous. Solid N-allylphthalimide (133 g, 0.71 mol) was then added over 10 minutes, keeping the exotherm generated under control. The solution was then stirred at this temperature for an additional 0.5 hour and poured into ice water (1.5 L). The mixture was extracted with ethyl acetate (3×1 L), dried (MgSO4), filtered and concentrated under reduced pressure. The crude solid was then purified through a silica gel plug (1 kg SiO2) from CH2Cl2 as the eluent. This afforded the desired 1,3-dioxane-4-ylmethylphthalimide as a white solid (95 g, 54%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×1 L)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude solid was then purified through a silica gel plug (1 kg SiO2) from CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-aacf1d808f2e492aacfd86618f30cb84
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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