2-(3-Methoxyphenyl)-2-methylpropanenitrile → 2-(3-Hydroxyphenyl)-2-methylpropanenitrile
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]=1Participants
3
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
- temperatureso maintained for 3 h
- temperatureAfter cooling
- customthe mixture was partitioned between DCM and water
- extractionfurther extracted
- dry with materialthe combined organic extracts dried over Na2SO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-5d8160982a1a47b19d8710e5afb1e6d1
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07259266B2
Reaction notes
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