Piperidine → HCID 190343, compound

HRID 1606407Notes

Reaction equation

HRID 1606407 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])C=O)([CH3:4])([CH3:3])[CH3:2].[C:18]([O:24][CH2:25][CH3:26])(=[O:23])[CH2:19][C:20](O)=O.N1CCCCC1>N1C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:15])([CH3:17])[CH3:16])[C:12]=1[OH:13])[CH:20]=[CH:19][C:18]([O:24][CH2:25][CH3:26])=[O:23])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 70615Monoethyl malonateHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Product 1

HCID 190343HCID 190343, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl 3,5-di tert.butyl-4-hydroxycinnamate was prepared by heating a mixture of 33.0 grams of 3,5-di tert.butyl-4-hydroxybenzaldehyde, 55.0 grams of ethyl hydrogen malonate, 50 milliliters of pyridine, and 3 milliliters of piperidine at 90° to 95° C. for 7 hours. The reaction mixture was cooled to room temperature and the solid which precipitated was filtered off, washed with 5 percent hydrochloric acid, and dried. Thirty grams of product was obtained which melted at 149° to 152° C. Working up the filtrate yielded an additional 5.5 grams of product.

Workup

  1. temperatureby heating
  2. customthe solid which precipitated
  3. filtrationwas filtered off
  4. washwashed with 5 percent hydrochloric acid
  5. customdried

Sources & evidence

ORD record
ord-03937bc979da49779ab43861ab4ce694
Source dataset
uspto-grants-1976_04
Patent number
US03953398

Reaction notes

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