Methanol → 4-n-Pentylcyclohexylmethyl 2,3-dicyano-4-hydroxyphenyl ether

HRID 342323

Reaction equation

HRID 342323 reaction equation
[C:1]([C:3]1[C:9]([C:10]#[N:11])=[C:8]([OH:12])[CH:7]=[CH:6][C:4]=1[OH:5])#[N:2].[OH-].[K+].CO.CS(O[CH2:22][CH:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:25][CH2:24]1)(=O)=O>O.CN(C)C=O>[C:1]([C:3]1[C:9]([C:10]#[N:11])=[C:8]([OH:12])[CH:7]=[CH:6][C:4]=1[O:5][CH2:22][CH:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:25][CH2:24]1)#[N:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 784672,3-DicyanohydroquinoneHCID 541366984-n-Pentylcyclohexylmethyl methanesulfonate

Product 1

HCID 571636604-n-Pentylcyclohexylmethyl 2,3-dicyano-4-hydroxyphenyl etherYield 31.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

5.6 g of 2,3-dicyanohydroquinone and 4.6 g of 85%-potassium hydroxide were added to a mixture solvent to 15 ml of methanol and 60 ml of N,N-dimethylformamide, followed by heating to 50° C. to provide a solution. To the solution, 11.0 g of 4-n-pentylcyclohexylmethyl methanesulfonate was added, followed by stirring for 3 hours at 100° C. After the reaction, the reaction mixture was poured into cold water and washed with ether. The water layer was acidified with 6N-hydrochloric acid aqueous solution until a pH value of 1 was shown, and was subjected to extraction with ether. The organic layer was washed successively with 5%-sodium hydrogenecarbonate aqueous solution and water, followed by drying with anhydrous magnesium sulfate and distilling-off of the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: toluene-ethyl acetate) and treated with activated carbon, followed by recrystallization from methanol to obtain 3.6 g of 4-n-pentylcyclohexylmethyl 2,3-dicyano-4-hydroxyphenyl ether.

Workup

  1. customto provide a solution
  2. customAfter the reaction
  3. washwashed with ether
  4. extractionwas subjected to extraction with ether
  5. washThe organic layer was washed successively with 5%-sodium hydrogenecarbonate aqueous solution and water
  6. dry with materialby drying with anhydrous magnesium sulfate and distilling-off of the solvent
  7. customto obtain a crude product
  8. customThe crude product was purified by silica gel column chromatography (eluent: toluene-ethyl acetate)
  9. additiontreated with activated carbon
  10. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-1126fd8da92e42228ed29f04b0ca053c
Source dataset
uspto-grants-1999_01
Patent number
US05858269

Linked notes

Loading…