3-[(4-Methoxyphenyl)methylene]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one → HCID 53977839, compound

HRID 1995896Notes

Reaction equation

HRID 1995896 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:6]([CH:7]=[C:8]2[CH:13]3[C:14]([CH3:16])([CH3:15])[C:10]([CH3:17])([CH2:11][CH2:12]3)[C:9]2=[O:18])=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[C:8]2[CH:13]3[C:14]([CH3:16])([CH3:15])[C:10]([CH3:17])([CH2:11][CH2:12]3)[C:9]2=[O:18])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6229773-[(4-Methoxyphenyl)methylene]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-oneHCID 10176127Pyridinium chloride

Product 1

HCID 53977839HCID 53977839, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 172 g of 3-(p-methoxybenzylidene)-bornan-2-one and 344 g of dry pyridine hydrochloride is heated under gentle reflux for 2 hours. After cooling, the reaction mixture is poured into 1 liter of water; the resulting solid precipitate, which is beige in colour, is filtered off, washed copiously with water and drained; it is then crystallised from 700 ml of isopropanol. 136 g of compound no. 2, which melts at 220°, are thus collected.

Workup

  1. temperatureis heated
  2. temperatureunder gentle reflux for 2 hours
  3. temperatureAfter cooling
  4. filtrationis filtered off
  5. washwashed copiously with water
  6. customit is then crystallised from 700 ml of isopropanol
  7. custom2, which melts at 220°, are thus collected

Sources & evidence

ORD record
ord-174c5a0aceb3404b91d4605b0b43d420
Source dataset
uspto-grants-1983_09
Patent number
US04406880

Reaction notes

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