Water → 2-(2,3-Dihydro-1,4-benzodioxin-6-yl)acetonitrile

HRID 401547Notes

Reaction equation

HRID 401547 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:6]2[O:7][CH2:8][CH2:9][O:10][C:5]=2[CH:4]=1.[C-:13]#[N:14].[Na+].O>CS(C)=O>[O:7]1[CH2:8][CH2:9][O:10][C:5]2[CH:4]=[C:3]([CH2:2][C:13]#[N:14])[CH:12]=[CH:11][C:6]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 52302876-(Chloromethyl)-2,3-dihydro-1,4-benzodioxine

Product 1

HCID 47373462-(2,3-Dihydro-1,4-benzodioxin-6-yl)acetonitrileYield 86%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 6-chloromethyl-2,3-dihydro-benzo[1,4]dioxine (12.5 g, 67.7 mmol) and NaCN (4.30 g, 87.8 mmol) in DMSO (50 mL) was stirred at rt for 1 h. The mixture was poured into water (150 mL) and then extracted with dichloromethane (50 mL×4). The combined organic layers were washed with water (50 mL×2) and brine (50 mL), dried over Na2SO4 and concentrated to dryness. The residue was purified by column (Petroleum Ether/Ethyl Acetate 50:1) on silica gel to obtain 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acetonitrile as a yellow oil (10.2 g, 86%). 1H-NMR (300 MHz, CDCl3) δ 6.78-6.86 (m, 3H), 4.25 (s, 4H), 3.63 (s, 2H).

Workup

  1. extractionextracted with dichloromethane (50 mL×4)
  2. washThe combined organic layers were washed with water (50 mL×2) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by column (Petroleum Ether/Ethyl Acetate 50:1) on silica gel

Sources & evidence

ORD record
ord-2b35e435066a4714aa0fa0f6b31571c8
Source dataset
uspto-grants-2014_06
Patent number
US08741933B2

Reaction notes

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