Acetic Anhydride → HCID 2755283, compound

HRID 1842976Notes

Reaction equation

HRID 1842976 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:15](OC(=O)C)(=O)C>CS(C)=O.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10](=[CH2:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 270191Methyl p-nitrophenylacetate

Product 1

HCID 2755283HCID 2755283, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 2-(4-nitrophenyl)acetate (8.0 g, 40.994 mmol, 1.0 eq) in DMSO (40 mL) was added tetramethyldiaminomethane (8.38 mL, 61.491 mmol, 1.5 eq) followed by acetic anhydride (12.78 mL, 135.17 mmol, 3.3 eq) at RT and the mixture was stirred for 2 h. The reaction mixture was diluted with water (40 mL), extracted with ether (80 mL×2) and the solvent evaporated. The crude product was purified by CC using EtOAc/PE (1:9) as eluent) to get methyl 2-(4-nitrophenyl)acrylate (4.0 g, 47%, solid; TLC system: EtOAc/PE (3:7), Rf: 0.60).

Workup

  1. extractionextracted with ether (80 mL×2)
  2. customthe solvent evaporated
  3. customThe crude product was purified by CC

Sources & evidence

ORD record
ord-f369d86bc87244efac6fb7cab62e6ac0
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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