Formaldehyde → HCID 59386295, compound

HRID 2095233Notes

Reaction equation

HRID 2095233 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:12]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[CH3:2].[CH2:24]=[O:25]>CS(C)=O.C(Cl)Cl>[OH:25][CH2:24][CH:1]([C:3]1[CH:4]=[C:5]([C:12]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[CH3:2]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 593862972-(3-Ethyl-4-nitrophenyl)-2-phenyl-1,3-dioxane

Product 1

HCID 59386295HCID 59386295, compoundYield 110.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 2-(3-ethyl-4-nitrophenyl)-2-phenyl-1,3-dioxane (17) (20.0 g, 63.8 mmol), paraformaldehyde (6.5 g, 72.6 mmol) and a methanolic solution of Triton B (35%, 17 mL) in DMSO (100 mL) was stirred for 2 hours at 85° C. The reaction mixture was then cooled to ambient temperature, diluted with CH2Cl2 (200 mL), washed with water (2×200 mL), partially concentrated in vacuo (for azeotropic drying) and filtered over silica gel (35 g). The filtrate was then evaporated in vacuo to give 24.15 g (approx. 70.3 mmol, 110%) of the crude product as a yellow oil.

Workup

  1. washwashed with water (2×200 mL)
  2. concentrationpartially concentrated in vacuo (for azeotropic drying)
  3. filtrationfiltered over silica gel (35 g)
  4. customThe filtrate was then evaporated in vacuo

Sources & evidence

ORD record
ord-2481a6c7256c4d0784cce4699e30f5c1
Source dataset
uspto-grants-2013_05
Patent number
US08445734B2

Reaction notes

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