O-Cresol → HCID 23001790, compound

HRID 398060Notes

Reaction equation

HRID 398060 reaction equation
[H-].[Na+].[C:3]1([CH3:10])[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:11][C:12]([CH3:17])=[CH:13][C:14](Cl)=[O:15].[Al+3].[Cl-].[Cl-].[Cl-]>CCCCCC.C1COCC1.C(Cl)Cl>[O:15]=[C:14]1[CH2:13][C:12]([CH3:17])([CH3:11])[C:7]2[C:8](=[C:3]([CH3:10])[CH:4]=[CH:5][CH:6]=2)[O:9]1

Participants

8

Reactant 4

HCID 335O-CresolHCID 24758Sodium hydrideHCID 1023943-Methyl-2-butenoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 23001790HCID 23001790, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 500 ml of round bottom flask, NaH (1.66 g, 60% suspension in oil, 0.046 mol) was washed with dry hexane. Then, dry THF (22 ml) was added followed by o-cresol (5 g, 0.046 mol) in 10 ml of dry THF. The reaction mixture was stirred at 0° C. for 30 min followed by addition of 3,3-dimethyl acryloyl chloride in 10 ml of THF. The resulting white slurry was stirred at room temperature for 12 h, then slowly quenched with water. The mixture was then extracted with ethyl acetate. The organic layer was washed with brine, water and dried over MgSO4. After filtration and removal of the solvent, a yellow oil was obtained (10.44 g). This oil was then dissolved in 50 ml of dry CH2Cl2, and was canulated into a solution of AlCl3 (10.8 g, 0.069 mmol) in 10 ml of CH2Cl2. The reaction mixture was stirred at room temperature for 12 h. Then ice-water was carefully added and the organic layer was separated, and washed with NaHCO3 (sat), brine, water and finally dried over MgSO4 After removal of the drying agent and solvent, the residue was purified by column chromatography (silica gel, ethyl acetate/hexane 1/9) to yield the title compound (4.408 g) as an oil.

Workup

  1. stirringThe resulting white slurry was stirred at room temperature for 12 h
  2. customslowly quenched with water
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washThe organic layer was washed with brine, water
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration and removal of the solvent
  7. customa yellow oil was obtained (10.44 g)
  8. stirringThe reaction mixture was stirred at room temperature for 12 h
  9. customthe organic layer was separated
  10. washwashed with NaHCO3 (sat), brine, water
  11. dry with materialfinally dried over MgSO4
  12. customAfter removal of the drying agent and solvent
  13. customthe residue was purified by column chromatography (silica gel, ethyl acetate/hexane 1/9)

Sources & evidence

ORD record
ord-2464a9eb89fa478aa49a4e798283c407
Source dataset
uspto-grants-2003_08
Patent number
US06610744B2

Reaction notes

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