Ethylene Glycol → 3-(2-Methyl-1,3-dioxolan-2-yl)benzonitrile

HRID 64227

Reaction equation

HRID 64227 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[C:5]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12])(=O)[CH3:6].CC1C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:6][C:5]1([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])[O:4][CH2:1][CH2:2][O:3]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 802223-Acetylbenzonitrile

Product 1

HCID 105595463-(2-Methyl-1,3-dioxolan-2-yl)benzonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
110 °C

Procedure

To the mixture of ethylene glycol (0.22 mL, 4 mmol), 3-acetylbenzonitrile 18 (300 mg, 2.04 mmol) and benzene (10 mL) in a Dean-Stark apparatus was added a catalytic amount of p-TSA (0.1 equiv). The reaction mixture was heated at 110° C. for 4 h. The benzene was removed under reduced pressure and the residue was purified by column chromatography using ethylacetate-hexane as an eluent to give 19 (293 mg, 76%). 1H NMR (CDCl3, 400 MHz) δ 2.62 (s, 4H), 7.59 (t, J=7.6 Hz, 1H), 7.82 (d, J=7.6 Hz, 1H)), 8.15 (d, J=8 Hz, 1H), 8.21 (s, 1H).

Workup

  1. customThe benzene was removed under reduced pressure
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ac30645f01914ab68e8cb78b3f297fff
Source dataset
uspto-grants-2016_09
Patent number
US09447134B2

Linked notes

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