P-Cresol → HCID 18960946, compound

HRID 1728444Notes

Reaction equation

HRID 1728444 reaction equation
[OH-].[K+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.S(C1C=CC(C)=CC=1)(O[CH2:15][C:16]1([CH3:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)(=O)=O>CO.[I-].[K+]>[CH3:15][C:16]1([CH2:22][O:10][C:7]2[CH:8]=[CH:9][C:4]([CH3:3])=[CH:5][CH:6]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 2879P-CresolHCID 14797Potassium HydroxideHCID 54059223HCID 54059223, compound

Product 1

HCID 18960946HCID 18960946, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 8.4 g (0.15 mole) of potassium hydroxide in 100 ml of MeOH was added 13.5 g (0.12 mole) of 4-methylphenol over a 15 minute period. The reaction was stirred at room temperature for 0.5 hour and MeOH was evaporated to afford a solid. A solution of this solid, 28.2 g (0.1 mole) of ((1-methyl)cyclohexyl)methyl tosylate and 1.4 g of potassium iodide were heated at 150° C. for 5 hours. The reaction was cooled to room temperature, poured onto ice-water and extracted with EtOAc. The EtOAc layer was washed with 2N aqueous NaOH, brine, dried over MgSO4, filtered and evaporated. The resulting oil was filtered through a plug of silica gel to give 20 g of product as an oil.

Workup

  1. customMeOH was evaporated
  2. customto afford a solid
  3. temperatureThe reaction was cooled to room temperature
  4. additionpoured onto ice-water
  5. extractionextracted with EtOAc
  6. washThe EtOAc layer was washed with 2N aqueous NaOH, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. filtrationThe resulting oil was filtered through a plug of silica gel

Sources & evidence

ORD record
ord-51abd0d144984548a25dca955e030434
Source dataset
uspto-grants-1994_07
Patent number
US05326905

Reaction notes

Loading…