1,3-Benzodioxole, 5-ethenyl- → 5-Ethylbenzo[d][1,3]dioxole

HRID 1476732Notes

Reaction equation

HRID 1476732 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1)=[CH2:2]>CO.[Pd]>[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 1389861,3-Benzodioxole, 5-ethenyl-

Product 1

HCID 115428085-Ethylbenzo[d][1,3]dioxoleYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-vinylbenzo[d][1,3]dioxole (6.0 g, 40.5 mmol) and 10% Pd/C (840 mg) in MeOH (50 mL) was hydrogenated for 8 h at 10 atm. Then Pd/C was filtered and the MeOH was removed to give compound 5-ethylbenzo[d][1,3]dioxole (3.0 g, 50%) as colorless liquid. 1H-NMR (DMSO-d6): δ 1.11 (t, 3H, J=7.2 Hz), 2.50 (q, 2H, J1=7.2 Hz, J2=16 Hz), 5.93 (s, 2H), 6.64 (d, 1H, J=8 Hz), 6.77 (m, 2H).

Workup

  1. filtrationThen Pd/C was filtered
  2. customthe MeOH was removed

Sources & evidence

ORD record
ord-11eb061cf0bb47e4a728f45cf72e0789
Source dataset
uspto-grants-2016_08
Patent number
US09402832B2

Reaction notes

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