Sodium Carbonate → N-(3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl)-2-propenamide

HRID 261740Notes

Reaction equation

HRID 261740 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[C:6]([C:10]1[CH:15]=[C:14]([NH2:16])[CH:13]=[C:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[OH:21])([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[C:6]([C:10]1[CH:15]=[C:14]([NH:16][C:1](=[O:4])[CH:2]=[CH2:3])[CH:13]=[C:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[OH:21])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 13140Acryloyl chlorideHCID 3142204-Amino-2,6-di-tert-butylphenol

Product 1

HCID 215005N-(3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl)-2-propenamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

N-(3,5-di tert.butyl-4-hydroxyphenyl)acrylamide was prepared by adding a solution of 10 grams of acryloyl chloride in 50 milliliters of benzene to a mixture of 22.1 grams of 2,6-di tert.butyl-4-aminophenol, 6 grams of sodium carbonate, and 100 milliliters of benzene. The addition was accomplished in 25 minutes at 19° C. to 38° C. The mixture was stirred for 21/2 hours and the precipitate which had formed was filtered off, washed thoroughly with water, and dried. The yield was 12.5 grams and the product melted at 204° C. to 206° C.

Workup

  1. additionThe addition
  2. customthe precipitate which had formed
  3. filtrationwas filtered off
  4. washwashed thoroughly with water
  5. customdried

Sources & evidence

ORD record
ord-c95994d653944ab4823bf3ab51ce9835
Source dataset
uspto-grants-1979_05
Patent number
US04152319

Reaction notes

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