1-Butanol → 4-Butoxymethyl-benzonitrile

HRID 1927264Notes

Reaction equation

HRID 1927264 reaction equation
[H-].[Na+].C1COCC1.[CH2:8]([OH:12])[CH2:9][CH2:10][CH3:11].[C:13]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1)#[N:14]>O.CN(C=O)C>[CH2:8]([O:12][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([C:13]#[N:14])=[CH:16][CH:17]=1)[CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 2631-ButanolHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 432676834-Butoxymethyl-benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of NaH (270 mg/66% in oil) and THF (20 mL) was added n-butanol (1.1 mL) at 0° C., which was stirred for 45 minutes at room temperature. The reaction mixture was cooled to 0° C., and a mixture of 4-cyanobenzyl bromide (1.5 g) and THF (10 mL) was added by drops thereto at the same temperature. The reaction mixture was stirred for 3 hours at room temperature, after which DMF (10 mL) was added to the reaction mixture, which was stirred for 4.5 hours at the same temperature. Water was added to the reaction mixture, which was then extracted with diethyl ether. The organic layer was washed with saturated brine, after which the solvent was evaporated from the organic layer under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:6) to obtain the titled compound (1.2 g).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. additionwas added by drops
  3. stirringThe reaction mixture was stirred for 3 hours at room temperature
  4. stirringwas stirred for 4.5 hours at the same temperature
  5. extractionwas then extracted with diethyl ether
  6. washThe organic layer was washed with saturated brine
  7. customafter which the solvent was evaporated from the organic layer under a reduced pressure
  8. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:6)

Sources & evidence

ORD record
ord-47eeccb980d84c57999a5f9d6c001e98
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

Loading…