Ethyl Methacrylate → Ethyl 2-methyl-3-(4-nitrophenyl)prop-2-enoate

HRID 1284863Notes

Reaction equation

HRID 1284863 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]([O:16][CH2:17][CH3:18])(=[O:15])[C:12]([CH3:14])=[CH2:13]>>[CH3:14][C:12](=[CH:13][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)[C:11]([O:16][CH2:17][CH3:18])=[O:15]

Participants

3

Reactant 2

HCID 7343Ethyl MethacrylateHCID 114661-Bromo-4-nitrobenzene

Product 1

HCID 54080096Ethyl 2-methyl-3-(4-nitrophenyl)prop-2-enoateYield 46%

Procedure

The procedure described in Example 26 is repeated, but using 5.05 g (25 mmols) of 4-bromonitrobenzene and 3.43 ml (27.5 mmols) of ethyl methacrylate. After a reaction time of 8 hours at 130° C. and working up as described in Example 1, recrystallising the crude product from methanol gives 2.70 g (11.5 mmols) of ethyl α-methyl-4-nitrocinnamate in the form of yellow crystals of melting point 75° C.; yield 46% of theory (conversion figure 4600; Pd content 0.01 mol %). Analysis for C12H13NO4 (molecular weight 235.24): calculated C 61.27; H 5.57; N 5.96, found C 61.18; H 5.57; N 6.24.

Workup

  1. customAfter a reaction time of 8 hours
  2. customat 130° C.
  3. customrecrystallising the crude product from methanol

Sources & evidence

ORD record
ord-65f543b111b84ea093c6780242c02b06
Source dataset
uspto-grants-1986_01
Patent number
US04564479

Reaction notes

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