Hydrochloric Acid → Camphor

HRID 359310Notes

Reaction equation

HRID 359310 reaction equation
[CH3:1][C@:2]12[C:10](=[O:11])[CH2:9][C@H:5]([C:6]1([CH3:8])[CH3:7])[CH2:4][CH2:3]2.[H-].[Na+].C(C1C=C(C=C(C(C)(C)C)C=1O)C=O)(C)(C)C.Cl>COCCOC.C(O)C.O>[C:2]12([CH3:1])[C:6]([CH3:8])([CH3:7])[CH:5]([CH2:4][CH2:3]1)[CH2:9][C:10]2=[O:11]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 159055D-Camphor

Product 1

HCID 2537CamphorYield 109.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

50 g (0.328 mol) of d-camphor are dissolved in 400 cm3 of 1,2-dimethoxyethane. 17.5 g of sodium hydride (0.73 mol) are added and the mixture is brought to reflux for one hour. 70 g (0.3 mol) of 3,5-di-tert-butyl-4-hydroxybenzaldehyde are added and the mixture is heated under reflux for 10 hours. After being cooled, the reaction medium is gradually diluted with 100 cm3 of ethanol and then with 100 cm3 of water. The mixture is acidified by adding 10% strength hydrochloric acid. The precipitate formed is filtered off, washed with water and dried. After recrystallization in isopropyl ether and then in ethanol, 54.5 g (49% yield) of expected product are obtained, possessing the following characteristics:

Workup

  1. temperatureto reflux for one hour
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 10 hours
  4. temperatureAfter being cooled
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. washwashed with water
  8. customdried
  9. customAfter recrystallization in isopropyl ether

Sources & evidence

ORD record
ord-6e8ec8bcd19146549eaad840b355e4fe
Source dataset
uspto-grants-1991_03
Patent number
US05000961

Reaction notes

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