Vanillin → HCID 21501233, compound

HRID 1658548Notes

Reaction equation

HRID 1658548 reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[CH3:12][NH:13][C:14]([NH:16][CH3:17])=[O:15].[P:18](OC1C=CC=CC=1)([O:26]C1C=CC=CC=1)[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1C=CC=CC=1>[CH3:12][N:13]1[C:14](=[O:15])[N:16]([CH3:17])[CH:2]([C:3]2[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=2)[P:18]1(=[O:26])[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 1183VanillinHCID 7293N,N'-DimethylureaHCID 7540Triphenyl phosphite

Product 1

HCID 21501233HCID 21501233, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 76.1g (0.5 mole) of vanillin, 44.0g (0.5 mole) of 1,3-dimethylurea, and 155.0g (0.5 mole) of triphenyl phosphite in 200g of benzene is stirred under N2 and warmed at reflux (95°) for 1 hr. About half of the benzene is distilled to give a yellow solution: 31P nmr -25.3 ppm. The reaction mixture solidifies while standing for several days. Additional benzene is added to aid in breaking up the solid. Filtration gives 64.0g of slightly yellow solid. Recrystallization of an 11.0g portion from acetonitrile gives 5.2g of white solid: mp 168°-170°; 31P nmr -24.5 ppm; molecular weight 362 (mass spectrum) (theory 362).

Workup

  1. temperaturewarmed
  2. temperatureat reflux (95°) for 1 hr
  3. distillationAbout half of the benzene is distilled
  4. customto give a yellow solution
  5. waitwhile standing for several days
  6. filtrationFiltration
  7. customgives 64.0g of slightly yellow solid
  8. customRecrystallization of an 11.0g portion from acetonitrile

Sources & evidence

ORD record
ord-107c53001e4745baa52f52f02a4e8e86
Source dataset
uspto-grants-1976_06
Patent number
US03965127

Reaction notes

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