Benzene → alpha-Sec-butyl-2-naphthaleneacetonitrile

HRID 261143Notes

Reaction equation

HRID 261143 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]#[N:13].Br[CH:15]([CH2:17][CH3:18])[CH3:16].C1C=CC=CC=1.[OH-].[Na+]>CCOCC.C1CC2OCCOCCOC3C(OCCOCCOC2CC1)CCCC3>[CH:15]([CH:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:12]#[N:13])([CH2:17][CH3:18])[CH3:16]

Participants

7

Reactant 4

HCID 241BenzeneHCID 65542-BromobutaneHCID 14798Sodium HydroxideHCID 820082-Naphthylacetonitrile

Product 1

HCID 20395159alpha-Sec-butyl-2-naphthaleneacetonitrileYield 86%

Reagents, catalysts & solvents 2

HCID 85955Dicyclohexano-18-crown-6CatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-naphthaleneacetonitrile (30.00 g, 0.179 mole), dicyclohexyl-18-crown-6 [1.60 g, 0.0043 mole (2.4 mole %)], 2-bromobutane (50.20 g, 0.366 mole), benzene (80 ml) and sodium hydroxide solution (50%, 80 ml) is stirred at room temperature for 16 hours. The organic layer is diluted with ether (250 ml), separated, washed successively with water, dilute hydrochloric acid and water and dried over sodium sulfate. Evaporation and distillation under vacuum gives α-sec-butyl-2-naphthaleneacetonitrile (34.3 g, 86%); b.p. 130° C. (0.1 mm).

Workup

  1. customseparated
  2. washwashed successively with water, dilute hydrochloric acid and water
  3. dry with materialdried over sodium sulfate
  4. customEvaporation and distillation under vacuum

Sources & evidence

ORD record
ord-f7d416b44d9c437abf114f79313241fb
Source dataset
uspto-grants-1979_08
Patent number
US04164415

Reaction notes

Loading…