Water → 2-(7-Methoxybenzo[d][1,3]dioxol-5-yl)acetonitrile

HRID 1879870Notes

Reaction equation

HRID 1879870 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([O:12][CH3:13])[C:6]2[O:10][CH2:9][O:8][C:7]=2[CH:11]=1.[C-:14]#[N:15].[Na+].O>CS(C)=O>[CH3:13][O:12][C:5]1[C:6]2[O:10][CH2:9][O:8][C:7]=2[CH:11]=[C:3]([CH2:2][C:14]#[N:15])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 139140006-(Chloromethyl)-4-methoxy-2H-1,3-benzodioxole

Product 1

HCID 139140012-(7-Methoxybenzo[d][1,3]dioxol-5-yl)acetonitrileYield 60.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-(chloromethyl)-4-methoxybenzo[d][1,3]dioxole (10.2 g, 40 mmol) in DMSO (100 mL) was added NaCN (2.43 g, 50 mmol) at room temperature. The mixture was stirred for 3 h and poured into water (500 mL). The aqueous phase was extracted with EtOAc (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated to give the crude product, which was washed with ether to afford 2-(7-methoxybenzo[d][1,3]dioxol-5-yl)acetonitrile (4.6 g, 45%). 1H NMR (400 MHz, CDCl3) δ 6.49 (s, 2H), 5.98 (s, 2H), 3.91 (s, 3H), 3.65 (s, 2H). 13C NMR (400 MHz, CDCl3) δ 148.9, 143.4, 134.6, 123.4, 117.3, 107.2, 101.8, 101.3, 56.3, 23.1.

Workup

  1. extractionThe aqueous phase was extracted with EtOAc (100 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. customevaporated
  4. customto give the crude product, which
  5. washwas washed with ether

Sources & evidence

ORD record
ord-4f91c5f732e24b248b406548bff87501
Source dataset
uspto-grants-2012_11
Patent number
US08318733B2

Reaction notes

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