Acetic Acid → Methyl 2-(2-nitrobenzylidene)-4,4-dimethoxyacetoacetate

HRID 1164634Notes

Reaction equation

HRID 1164634 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[CH3:12][O:13][CH:14]([O:22][CH3:23])[C:15](=[O:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18].C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[C:16]([C:15]([CH:14]([O:13][CH3:12])[O:22][CH3:23])=[O:21])[C:17]([O:19][CH3:20])=[O:18])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 111012-NitrobenzaldehydeHCID 11008445Methyl 4,4-dimethoxy-3-oxobutanoate

Product 1

HCID 53644054Methyl 2-(2-nitrobenzylidene)-4,4-dimethoxyacetoacetateYield 109.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 2-nitrobenzaldehyde (6.8009 g), methyl 4,4-dimethoxyacetoacetate (8.7204 g), acetic acid (0.5405 g) and piperidine (0.4598 g) in benzene (30 ml) was heated to reflux for 2 hours under azeptropic dehydration. The reation mixture was diluted with benzene (100 ml), washed twice with water, and in turn with diluted aqueous sodium bicarbonate solution and water, dried over magnesium sulfate and evaporated to dryness under reduced pressure to give crude oily methyl 2-(2-nitrobenzylidene)-4,4-dimethoxyacetoacetate (15.23 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours under azeptropic dehydration
  3. washwashed twice with water
  4. dry with materialin turn with diluted aqueous sodium bicarbonate solution and water, dried over magnesium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8a518878760240f8aa2c24698f4e836c
Source dataset
uspto-grants-1983_01
Patent number
US04370334

Reaction notes

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