Formaldehyde → HCID 118308739, compound

HRID 923477Notes

Reaction equation

HRID 923477 reaction equation
[N+:1]([CH:4]([C:6]1[CH:15]=[CH:14][C:9]([C:10](OC)=[O:11])=[CH:8][CH:7]=1)[CH3:5])([O-:3])=[O:2].[CH2:16]=[O:17].C[O-].[Na+].[Cl-].[NH4+].CN([CH:26]=[O:27])C>>[OH:17][CH2:16][C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:27][CH3:26])=[O:11])=[CH:14][CH:15]=1)([N+:1]([O-:3])=[O:2])[CH3:5]

Participants

6

Reactant 5

HCID 712FormaldehydeHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 11310314Benzoic acid, 4-(1-nitroethyl)-, methyl ester

Product 1

HCID 118308739HCID 118308739, compound

Procedure

To a mixture of 1.44 g of methyl 4-(1-nitroethyl)benzoate and 29 ml of DMF were added 612 mg of paraformaldehyde and 150 mg of sodium methoxide, followed by stirring at room temperature for 18 hours. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was then evaporated. The obtained residue was purified by silica gel column chromatography to obtain 730 mg of methyl 4-(1-hydroxy-2-nitropropan-2-yl)benzoate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was then evaporated
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-023dd66e6e8245c3929d6f5539798d8c
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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