3-Bromo-1-propanol → 4-(3-Hydroxypropoxy)benzonitrile

HRID 2078432Notes

Reaction equation

HRID 2078432 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][OH:14].[OH-].[Na+]>C1(C)C=CC=CC=1>[OH:14][CH2:13][CH2:12][CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 123083-Bromo-1-propanolHCID 130194-CyanophenolHCID 14798Sodium Hydroxide

Product 1

HCID 151263514-(3-Hydroxypropoxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
67.5 °C

Procedure

To a flask was added 4-hydroxybenzonitrile (50 g, 0.41 mol, 1 eq.) and toluene (400 mL). The resulting mixture was heated to 65° C.±5° C. To the stirring reaction mixture was added 3-bromo-1-propanol (72.90 g, 0.51 mol, 1.25 eq.) and then, over the course of 20 minutes, sodium hydroxide (210 mL, 2.5 M, 0.52 mol, 1.25 eq.). The reaction was heated to 65 to 70° C. for 17 hours. The aqueous layer was separated from the organic layer at 60 to 65° C. The organic layer was then employed directly in the next step without further purification. LC purity 95.3%.

Workup

  1. temperatureThe resulting mixture was heated to 65° C.±5° C
  2. customTo the stirring reaction mixture
  3. customThe aqueous layer was separated from the organic layer at 60 to 65° C
  4. customThe organic layer was then employed directly in the next step without further purification

Sources & evidence

ORD record
ord-cdfd90d926914ebd92cbca0ac4feda33
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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