2-(3-Methoxyphenyl)-2-methylpropanenitrile → 2-(3-Hydroxyphenyl)-2-methylpropanenitrile

HRID 854963Notes

Reaction equation

HRID 854963 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.Cl.[NH+]1C=CC=CC=1>>[OH:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 101301932-(3-Methoxyphenyl)-2-methylpropanenitrileHCID 21584435Pyridinium hydrochloride

Product 1

HCID 125381552-(3-Hydroxyphenyl)-2-methylpropanenitrile

Conditions

Temperature
210 °C

Procedure

A mixture of the title product of Example 106 Step 1 (520 mg, 2.97 mmoles) and pyridinium hydrochloride (2 g, 17.3 mmol) was stirred in an oil bath at 200-220 ° C. under a drying tube and so maintained for 3 h. After cooling, the mixture was partitioned between DCM and water, further extracted, and the combined organic extracts dried over Na2SO4, filtered, and evaporated to give the title compound, 416 mg, as a brownish oil.

Workup

  1. temperatureso maintained for 3 h
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between DCM and water
  4. extractionfurther extracted
  5. dry with materialthe combined organic extracts dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-5d8160982a1a47b19d8710e5afb1e6d1
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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