P-Cresol → HCID 2063533, compound

HRID 986556Notes

Reaction equation

HRID 986556 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[CH2:10]([N+:17](C)(C)C)[C:11]1C=CC=C[CH:12]=1>C(#N)C=C.CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:11][C:10]#[N:17])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2879P-CresolHCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 2063533HCID 2063533, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7855AcrylonitrileSolvent

Procedure

A solution of 4-methylphenol, (20.0 g 0.185 moles), in acrylonitrile, (150 ml), was treated with benzyltrimethylammonium hydroxide, 40% in methanol (Triton B), (6 ml) and the reaction refluxed for 10 hours, then cooled, and evaporated in vacuo. The residual oil was partitioned between diethyl ether and water and the organic phase separated and washed with water, dilute sodium hydroxide solution, dilute hydrochloric acid, brine and dried (MgSO4). Evaporation of the solvent in vacuo gave 23.44 g of crude product, which was recrystallized from petroleum ether 60°-80° C./diethyl ether to yield 22.93 g, (76%) of pure product as a white crystalline solid, mp 47°-8° C.

Workup

  1. temperaturethe reaction refluxed for 10 hours
  2. temperaturecooled
  3. customevaporated in vacuo
  4. customThe residual oil was partitioned between diethyl ether and water
  5. customthe organic phase separated
  6. washwashed with water, dilute sodium hydroxide solution, dilute hydrochloric acid, brine
  7. dry with materialdried (MgSO4)
  8. customEvaporation of the solvent in vacuo
  9. customgave 23.44 g of crude product, which
  10. customwas recrystallized from petroleum ether 60°-80° C./diethyl ether

Sources & evidence

ORD record
ord-a8b712cdf9104bc5a9824950c2d3a68a
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

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