Methyl Isobutyl Ketone → 4-(3-Hydroxypropoxy)benzonitrile

HRID 2078431Notes

Reaction equation

HRID 2078431 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C[CH:17](C)[CH2:18][C:19](=[O:21])C.BrCCCO>O>[OH:21][CH2:19][CH2:18][CH2:17][O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 130194-Cyanophenol

Product 1

HCID 151263514-(3-Hydroxypropoxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask was added 4-hydroxybenzonitrile (50 g, 0.41 mol, 1 eq.) and potassium carbonate (0.51 mol, 1.25 eq.). To this mixture was added 4-methyl-2-pentanone (400 mL). Stirring was started and 3-bromo-1-propanol (61.50 g, 0.4 mol, 1.05 eq.) was added in one portion. The reaction mixture was heated to between 85 and 90° C. for 5 hours. Water (250 mL) was then added and the resultant mixture heated to 30° C. until all solids had gone into solution. The aqueous layer was separated from the organic layer. The organic layer was diluted with 4-methyl-2-pentanone (400 mL) to provide a solution of the sub-title compound that was employed directly in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated to between 85 and 90° C. for 5 hours
  2. customThe aqueous layer was separated from the organic layer
  3. additionThe organic layer was diluted with 4-methyl-2-pentanone (400 mL)

Sources & evidence

ORD record
ord-e4f995185e6c441484a378d7926b0bba
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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