Benzene → alpha-Sec-butyl-2-naphthaleneacetonitrile

HRID 2071323Notes

Reaction equation

HRID 2071323 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-5a9cb4d2182a4d6e947fe79ea72f38de
Source dataset
uspto-grants-1977_09
Patent number
US04046799

Reaction notes

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