Toluene → HCID 19937045, compound

HRID 1682249Notes

Reaction equation

HRID 1682249 reaction equation
C([C:4]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:5]=1[CH:6]=O)C=C.[C:16]([O:30][CH2:31][CH:32]([CH2:37][CH3:38])[CH2:33][CH2:34][CH2:35][CH3:36])(=[O:29])[CH2:17][C:18]([O:20][CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26])=[O:19].[C:39]1(C)[CH:44]=CC=C[CH:40]=1.N1CCCCC1>C(O)(=O)C>[CH2:44]([C:11]1[CH:4]=[C:5]([CH:8]=[C:9]([O:14][CH3:15])[C:10]=1[O:12][CH3:13])[CH:6]=[C:17]([C:18]([O:20][CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26])=[O:19])[C:16]([O:30][CH2:31][CH:32]([CH2:37][CH3:38])[CH2:33][CH2:34][CH2:35][CH3:36])=[O:29])[CH:39]=[CH2:40]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8082PiperidineHCID 9923500di-(2-ethylhexyl) malonateHCID 11217997HCID 11217997, compound

Product 1

HCID 19937045HCID 19937045, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3™allyl-4,5-dimethoxybenzaldehyde (10.3 g, 0.05 moles), di-(2-ethylhexyl) malonate (16.4 g, 0.05 moles), toluene (20 ml), acetic acid (0.41 ml) and piperidine (0.77 ml) is heated to reflux using a Dean Stark. After cooling, washing the toluene phase with water, drying and evaporation of the solvent, an orange-coloured oil is obtained, which is purified by chromatography on a column of silica 60 (eluent: 90:10 heptane/ethyl acetate) to give di-(2-ethylhexyl) 3-allyl-4,5-dimethoxybenzalmalonate (colourless oil, 15 g, yield=64%), which has the following characteristics:

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. washwashing the toluene phase with water
  5. customdrying
  6. customevaporation of the solvent
  7. customan orange-coloured oil is obtained
  8. customwhich is purified by chromatography on a column of silica 60 (eluent: 90:10 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-d725a560384140638fb515d85c326714
Source dataset
uspto-grants-1992_12
Patent number
US05175340

Reaction notes

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