Hydrochloric Acid → HCID 54565851, compound

HRID 1606410Notes

Reaction equation

HRID 1606410 reaction equation
[CH3:1][C:2]([C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([C:16]([CH3:21])([CH3:20])[CH2:17][CH2:18][CH3:19])[C:14]=1[OH:15])[CH:10]=O)([CH3:6])[CH2:3][CH2:4][CH3:5].[C:22]([O:28][CH2:29][CH3:30])(=[O:27])[CH2:23]C(O)=O.N1CCCCC1.Cl>O.N1C=CC=CC=1>[CH3:20][C:16]([C:13]1[CH:12]=[C:9]([CH:8]=[C:7]([C:2]([CH3:6])([CH3:1])[CH2:3][CH2:4][CH3:5])[C:14]=1[OH:15])[CH:10]=[CH:23][C:22]([O:28][CH2:29][CH3:30])=[O:27])([CH3:21])[CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 70615Monoethyl malonateHCID 20371372HCID 20371372, compound

Product 1

HCID 54565851HCID 54565851, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Ethyl 3,5-bis(1,1-dimethylbutyl)-4-hydroxycinnamate was prepared by heating a mixture of 29 grams of 3,5-bis(1,1-dimethylbutyl)-4-hydroxybenzaldehyde, 40 grams of ethyl hydrogen malonate, 50 milliliters pyridine and 3 milliliters of piperidine at 90° to 95° C. for 7 hours. The reaction mixture was poured into a solution of 50 milliliters of concentrated hydrochloric acid in 100 milliliters of water. The oil which precipitated was separated by extraction with petroleum ether and the extract was stripped under vacuum to a pot temperature of 50°C./14 mm. The viscous residue weighed 39 grams.

Workup

  1. temperatureby heating
  2. customThe oil which precipitated
  3. customwas separated by extraction with petroleum ether
  4. customwas stripped under vacuum to a pot temperature of 50°C./14 mm

Sources & evidence

ORD record
ord-a8daa66ff8994df1b664c627fa69e08c
Source dataset
uspto-grants-1976_04
Patent number
US03953398

Reaction notes

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