2-Bromopropane → 2-(4-Methoxyphenyl)-3-methylbutyronitrile

HRID 2050084Notes

Reaction equation

HRID 2050084 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[N:13])=[CH:7][CH:6]=1.[CH2:14]1[CH2:19]C2OCCOCCOC3C(OCCOCCOC2C[CH2:15]1)CCCC3.BrC(C)C>C1C=CC=CC=1>[CH:14]([CH:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=1)[C:12]#[N:13])([CH3:19])[CH3:15]

Participants

6

Reactant 4

HCID 63582-BromopropaneHCID 14798Sodium HydroxideHCID 66031Benzeneacetonitrile, 4-methoxy-HCID 85955Dicyclohexano-18-crown-6

Product 1

HCID 130590562-(4-Methoxyphenyl)-3-methylbutyronitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
45 °C

Procedure

A solution of sodium hydroxide (50%, 300 ml) is added to a solution of p-methoxyphenylacetonitrile (147 g, 1 mol), dicyclohexyl-18-crown-6 (18.63 g, 5 mol %), 2-bromopropane (320 g, 2.6 mol) and benzene (300 ml). The reaction mixture is heated to 45° C. and held for 4 days. The organic phase is separated, washed well with water (3×200 ml), dilute hydrochloric acid (1×200 ml), water (2×200 ml) and evaporated to an oil. Vacuum distillation gives the product (175.6 g, 81% real): boiling point 96° C. to 100° C. (0.15 mm); nmr (CDCl3) shows that the distilled material contains 12.5 mol % of the starting nitrile.

Workup

  1. customThe organic phase is separated
  2. washwashed well with water (3×200 ml), dilute hydrochloric acid (1×200 ml), water (2×200 ml)
  3. customevaporated to an oil
  4. distillationVacuum distillation
  5. customgives the product (175.6 g, 81% real)

Sources & evidence

ORD record
ord-ee3376f4c49b4074abcb7fcda549d973
Source dataset
uspto-grants-1980_04
Patent number
US04199595

Reaction notes

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