Sodium Carbonate → N-(3,5-di tert.butyl-4-hydroxyphenyl)cinnamamide

HRID 261744Notes

Reaction equation

HRID 261744 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:12]([C:16]1[CH:21]=[C:20]([NH2:22])[CH:19]=[C:18]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:17]=1[OH:27])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[C:23]([C:18]1[CH:19]=[C:20]([NH:22][C:1](=[O:10])[CH:2]=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:21]=[C:16]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:17]=1[OH:27])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 660233-Phenylprop-2-enoyl chlorideHCID 3142204-Amino-2,6-di-tert-butylphenol

Product 1

HCID 54273259N-(3,5-di tert.butyl-4-hydroxyphenyl)cinnamamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(3,5-di tert.butyl-4-hydroxyphenyl)cinnamamide was prepared by adding a solution of 18.2 grams of cinnamoyl chloride in 50 milliliters of benzene to a solution of 2,6-di tert.butyl-4 -aminophenol prepared as described in Example 2 to which had been added 6 grams of sodium carbonate. The addition was accomplished in 30 minutes at 24° C. to 37° C. The mixture was stirred for 1 hour. The solid product was filtered, washed thoroughly with 2% hydrochloric acid, and dried. The yield was 17 grams of product which melted at 211° C. to 214° C.

Workup

  1. customprepared
  2. additionThe addition
  3. filtrationThe solid product was filtered
  4. washwashed thoroughly with 2% hydrochloric acid
  5. customdried

Sources & evidence

ORD record
ord-37e3aa916e73406b961ed7e1c8862e08
Source dataset
uspto-grants-1979_05
Patent number
US04152319

Reaction notes

Loading…