Acrylamide → HCID 12682102, compound

HRID 981800Notes

Reaction equation

HRID 981800 reaction equation
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].CC1(C)O[C:11](=[O:13])[CH:10]=[C:9]([CH3:14])[O:8]1>C1(C)C(C)=CC=CC=1.C(OCCCC)(=O)C.C1(=O)C=CC(=O)C=C1>[C:11]([NH:5][C:1](=[O:4])[CH:2]=[CH2:3])(=[O:13])[CH2:10][C:9]([CH3:14])=[O:8]

Participants

6

Reactant 2

HCID 6579AcrylamideHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Product 1

HCID 12682102HCID 12682102, compoundYield 63.2%

Reagents, catalysts & solvents 3

HCID 4650QuinoneCatalystHCID 7237O-XyleneSolventHCID 31272Butyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of acrylamide (21.3 g, 0.3 mol), butylated hydroxytoluene (BHT, 0.66 g, 1%) and benzoquinone (BQ, 0.22 g, 0.7%) in a mixture of 75 mL of xylene and 150 mL of n-butyl acetate was heated to about 80° C. When the reaction mixture reached 80° C., 42.6 g (0.3 mol) of 2,2,6-trimethyl-4H-1,3-dioxin-4-one was added as a small stream over a period of about 10 minutes; the reaction mixture was then heated rapidly up to about 120° C., and maintained at that temperature for about 10 minutes. Once heating of the reaction mixture was complete, the reaction mixture was allowed to cool and 29.4 g (63% yield; mp 128° to 130° C.) of N-acetoacetyl acrylamide was collected as a white precipitate and air dryed.

Workup

  1. customreached 80° C.
  2. temperaturethe reaction mixture was then heated rapidly up to about 120° C.
  3. temperaturemaintained at that temperature for about 10 minutes
  4. temperatureOnce heating of the reaction mixture
  5. temperatureto cool

Sources & evidence

ORD record
ord-8641198e79e84f6caabbede6d3b3c6a5
Source dataset
uspto-grants-1991_02
Patent number
US04992584

Reaction notes

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