Acetone → 2-Hydroxy-3,3-dimethyl-2,3-dihydrobenzofuran-5-carbonitrile

HRID 444104Notes

Reaction equation

HRID 444104 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

HCID 180AcetoneHCID 205362092-Chloro-5-cyano-2,3-dihydro-3,3-dimethylbenzofuran

Product 1

HCID 205362002-Hydroxy-3,3-dimethyl-2,3-dihydrobenzofuran-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. custom2 hours
  2. extractionThe product was then extracted into diethyl ether
  3. washthe extracted solution then being washed twice with water
  4. dry with materialdried over sodium sulphate
  5. customto give 1.7 g of crude product
  6. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-86104d8d76674816a07b6d5b75e4df32
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

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