Hydrochloric Acid → Acrylanilide, 4'-hydroxy-2-methyl-

HRID 1070373Notes

Reaction equation

HRID 1070373 reaction equation
[C:1]([OH:6])(=O)[C:2]([CH3:4])=[CH2:3].C(OC(Cl)=O)C.C(N(CC)CC)C.[CH:20]1[C:25]([NH2:26])=[CH:24][CH:23]=[C:22]([OH:27])[CH:21]=1.Cl>C(#N)C>[OH:27][C:22]1[CH:23]=[CH:24][C:25]([NH:26][C:1](=[O:6])[C:2]([CH3:4])=[CH2:3])=[CH:20][CH:21]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4034-AminophenolHCID 4093Methacrylic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 29520Acrylanilide, 4'-hydroxy-2-methyl-Yield 56.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 1 liter flask 600 ml of acetonitrile, 95.2 g (1.1 mol) of methacrylic acid and 120.1 g (1.1 mol) of chloroformic acid ethyl ester were added. To this mixture 111.8 g (1.1 mol) of triethylamine was added over a period of 1 hour in cool bath. Stirring was continued for 1 hour at room temperature and 120.0 g (1 mol) of p-aminophenol was added. The mixture was heated for 5 hours at 5020 C. The mixture was poured into 5 liter of 1% HCl solution. The deposit was filtered, washed and dried to produce 99.35 g of N-(4-Hydroxyphenyl)methacrylamide.

Workup

  1. temperatureThe mixture was heated for 5 hours at 5020 C
  2. filtrationThe deposit was filtered
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-2e2b3a27e1ba4a3097dfde5714a97972
Source dataset
uspto-grants-2005_06
Patent number
US06902860B2

Reaction notes

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