Acetone → 2-Hydroxy-3,3-dimethyl-2,3-dihydrobenzofuran-5-carbonitrile
Reaction equation
Cl[CH:2]1[C:6]([CH3:8])([CH3:7])[C:5]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:4]=2[O:3]1.CC(C)=[O:17]>O>[C:13]([C:10]1[CH:11]=[CH:12][C:4]2[O:3][CH:2]([OH:17])[C:6]([CH3:8])([CH3:7])[C:5]=2[CH:9]=1)#[N:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The product of Example 45 (2 g) was boiled under reflux in water (5 ml) and acetone (15 ml) for 31/2 hours. The product was then extracted into diethyl ether, the extracted solution then being washed twice with water, dried over sodium sulphate and run down under vacuum to give 1.7 g of crude product. Recrystallisation from toluene gave pure title product (1.3 g), mp 127°-129° C.
Workup
- custom2 hours
- extractionThe product was then extracted into diethyl ether
- washthe extracted solution then being washed twice with water
- dry with materialdried over sodium sulphate
- customto give 1.7 g of crude product
- customRecrystallisation from toluene
Sources & evidence
- ORD record
- ord-86104d8d76674816a07b6d5b75e4df32
- Source dataset
- uspto-grants-1981_04
- Patent number
- US04263037
Reaction notes
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