Hydrochloric Acid → 3.5-Di tert.butyl-4-hydroxycinnamamide

HRID 1606409Notes

Reaction equation

HRID 1606409 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[C:18]([NH2:24])(=[O:23])[CH2:19]C(O)=O.N1CCCCC1.Cl>O.N1C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:16])([CH3:17])[CH3:15])[C:12]=1[OH:13])[CH:8]=[CH:19][C:18]([NH2:24])=[O:23])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 753673-Amino-3-Oxopropanoic Acid

Product 1

HCID 544743213.5-Di tert.butyl-4-hydroxycinnamamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

3.5-di tert.butyl-4-hydroxycinnamamide was prepared by heating a mixture of 23.4 grams of 3,5-di tert.butyl-4-hydroxybenzaldehyde, 31 grams of malonic acid monoamide, 75 milliliters of pyridine, and 3 milliliters of piperidine at 90° to 100° C. for 101/2 hours. The reaction mixture was poured into a solution of 75 milliliters of concentrated hydrochloric acid and 100 milliliters of water. The solid which precipitated was filtered off, dried, and recrystallized from benzene. Ten grams of product was obtained which melted at 217° to 219° C.

Workup

  1. temperatureby heating
  2. customThe solid which precipitated
  3. filtrationwas filtered off
  4. customdried
  5. customrecrystallized from benzene

Sources & evidence

ORD record
ord-9e422c735a5c4b07b9bab60a3d565cd8
Source dataset
uspto-grants-1976_04
Patent number
US03953398

Reaction notes

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