2,6-Di-tert-butyl-4-methylphenol → 2-({[2-(Methylsulphanyl)phenyl]carbamoyl}oxy)butyl prop-2-enoate

HRID 1514830Notes

Reaction equation

HRID 1514830 reaction equation
C(C1C=C(C)C=C(C(C)(C)C)C=1[OH:16])(C)(C)C.CN(CCCN1CN(CCCN(C)C)CN(CCCN(C)C)C1)C.[CH3:41][S:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[N:49]=[C:50]=[O:51].[C:52]([O:56][CH2:57][CH2:58][CH:59](O)[CH3:60])(=[O:55])[CH:53]=[CH2:54].[N-]=C=O>C(OCC)(=O)C>[C:52]([O:56][CH2:57][CH:58]([O:51][C:50](=[O:16])[NH:49][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=1[S:42][CH3:41])[CH2:59][CH3:60])(=[O:55])[CH:53]=[CH2:54]

Participants

7

Reactant 5

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 85160N,N',N''-Tris(3-dimethylaminopropyl)hexahydro-S-triazineHCID 105034IsocyanateHCID 27369891-Isocyanato-2-(methylsulfanyl)benzeneHCID 139321793-Hydroxybutyl acrylate

Product 1

HCID 685530972-({[2-(Methylsulphanyl)phenyl]carbamoyl}oxy)butyl prop-2-enoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

0.008 g of 2,6-di-tert-butyl-4-methylphenol, 0.004 g of Desmorapid Z, 4.3 g of 2-(methylthio)phenyl isocyanate in 8.5 g ethyl acetate were initially introduced into a 50 ml round-bottomed flask and heated to 60° C. Thereafter, 4 g of 3-hydroxybutyl acrylate were added dropwise and the mixture was kept further at 60° C. until the isocyanate content had fallen below 0.1%. Thereafter, the ethyl acetate was distilled off at 5 mbar and cooling was effected. The product was obtained as a light yellow liquid.

Workup

  1. distillationThereafter, the ethyl acetate was distilled off at 5 mbar
  2. temperaturecooling
  3. customThe product was obtained as a light yellow liquid

Sources & evidence

ORD record
ord-1ee0a09797034870911f45a192c71b4f
Source dataset
uspto-grants-2012_07
Patent number
US08222314B2

Reaction notes

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