4-Cyanophenol → Isopropyl alcohol isopropyl ether

HRID 261070

Reaction equation

HRID 261070 reaction equation
S1C2CN[CH2:8][CH2:9][C:4]=2C=C1.C(C1C=[CH:16][C:15]([OH:18])=[CH:14]C=1)#N>O1CCOCC1>[CH:15]([O:18][CH:9]([CH3:8])[CH3:4])([CH3:16])[CH3:14].[CH:15]([OH:18])([CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 130194-CyanophenolHCID 123370254H,5H,6H,7H-thieno(2,3-c)pyridineHCID 178486302HCID 178486302, compound

Product 1

HCID 21202047Isopropyl alcohol isopropyl etherYield 23%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4,5,6,7-tetrahydro-thieno[2,3-c]pyridine (1 g; 7.2 mmoles), p-cyano-phenol (95% purity; 0.9 g; 7.2 mmoles), polyoxymethylene (0.43 g; 14.4 mmoles) and dioxan (20 cc) is stirred at 80° C. during 4 hours. After concentration in vacuo, the residue is taken up into 2N hydrochloric acid. The aqueous phase is extracted with ether, made basic with concentrated ammonia and again extracted with methylene chloride. The organic extracts are washed with water, dried over sodium sulfate and concentrated in vacuo. The residue is recrystallized from isopropyl ether-isopropanol (M.p. 134° C.; yield: 23%).

Workup

  1. concentrationAfter concentration in vacuo
  2. extractionThe aqueous phase is extracted with ether
  3. extractionagain extracted with methylene chloride
  4. washThe organic extracts are washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fefc21f9657424996b491b80f457b88
Source dataset
uspto-grants-1979_08
Patent number
US04163852

Linked notes

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