Hydrochloric Acid → HCID 54238737, compound

HRID 1606411Notes

Reaction equation

HRID 1606411 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]([CH2:24]C(O)=O)#[N:23].N1CCCCC1.Cl>O.N1C=CC=CC=1>[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]=[CH:24][C:22]#[N:23])([CH3:6])[CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 9740Cyanoacetic acidHCID 20371372HCID 20371372, compound

Product 1

HCID 54238737HCID 54238737, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

3,5-bis(1,1-dimethylbutyl)-4-hydroxycinnamonitrile was prepared by heating a mixture of 29 grams of 3,5-bis(1,1-dimethylbutyl)-4-hydroxybenzaldehyde, 25.5 grams of cyanoacetic acid, 75 milliliters of pyridine, and 3 milliliters of piperidine at 95° to 100° 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./13 mm. The residue, which weighed 32 grams, was a viscous liquid which crystallized slowly on standing.

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./13 mm
  5. customcrystallized slowly

Sources & evidence

ORD record
ord-3f95724806394d5d8967457d185a3932
Source dataset
uspto-grants-1976_04
Patent number
US03953398

Reaction notes

Loading…