Toluene → HCID 19937045, compound

HRID 344631Notes

Reaction equation

HRID 344631 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[CH:7]=O)[CH:2]=[CH2:3].[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].C1(C)C=CC=CC=1.N1CCCCC1>C(O)(=O)C>[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[CH:7]=[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:2]=[CH2:3]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8082PiperidineHCID 31440593-Allyl-4,5-dimethoxy-benzaldehydeHCID 9923500di-(2-ethylhexyl) malonate

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 mole), of di-(2-ethylhexyl) malonate (16.4 g, 0.05 mole), of toluene (20 ml), of acetic acid (0.41 ml) and of piperidine (0.77 ml) was heated at reflux for 5 hours with a Dean Stark. After cooling, washing the toluene phase with water, drying and evaporating off the solvent, an orange-colored oil was obtained, which was 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 (colorless oil, 15 g, yield=64%) which had the following characteristics:

Workup

  1. temperatureat reflux for 5 hours with a Dean Stark
  2. temperatureAfter cooling
  3. washwashing the toluene phase with water
  4. customdrying
  5. customevaporating off the solvent
  6. customan orange-colored oil was obtained
  7. customwhich was purified by chromatography on a column of silica 60 (eluent: 90.10 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-b01eeb22940641c59449f81f3156f927
Source dataset
uspto-grants-1991_10
Patent number
US05053290

Reaction notes

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