2,4,6-Trimethylphenol → HCID 53835720, compound

HRID 1076792Notes

Reaction equation

HRID 1076792 reaction equation
[C:1]1([CH3:10])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1O.[H-].[Na+].Br[CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18].[OH-:19].[K+]>C1C=CC=CC=1.CCCCCC>[CH3:14][C:15]12[CH2:8][CH:3]3[CH:2]([C:1]([CH3:10])=[CH:6]1)[C:17]([CH3:18])([CH2:7][CH2:5][CH2:4]3)[C:16]2=[O:19]

Participants

7

Reactant 4

HCID 106982,4,6-TrimethylphenolHCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 707041-Pentene, 5-bromo-

Product 1

HCID 53835720HCID 53835720, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8058HexaneSolvent

Procedure

6.8 g. of mesitol dissolved in 50 ml of benzene are treated with 2.4 g of sodium hydride (50 percent suspension in oil). After completion of the salt-formation, 8.5 g of 5-bromo-1-pentene are added thereto. The reaction mixture is heated at reflux for 24 hours, taken up in hexane and shaken with an aqueous potassium hydroxide solution (10 percent by weight) and Claisen's alkali (35 g of KOH, 25 ml of water and 100 ml of methanol). The organic phase is dried, evaporated and chromatographed on silicagel using hexane and 3 percent diethylether in hexane as the elution agent. Evaporation of the eluate and recrystallization of the residue from hexane yields 1,3,9-trimethyl-tricyclo [5,3,1,03,8 ] undeca-9-en-2-one of melting point 46° -47°C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 24 hours
  3. customThe organic phase is dried
  4. customevaporated
  5. customchromatographed on silicagel
  6. customEvaporation of the eluate and
  7. customrecrystallization of the residue from hexane

Sources & evidence

ORD record
ord-cc23197590f9479293d27ee107ed3698
Source dataset
uspto-grants-1976_05
Patent number
US03957878

Reaction notes

Loading…