Allyl bromide → Methyl 3-(allyloxy)benzoate

HRID 2180241Notes

Reaction equation

HRID 2180241 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.[CH2:12](Br)[CH:13]=[CH2:14].CC(C)([O-])C.[K+]>CS(C)=O>[CH2:14]([O:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([O:2][CH3:1])=[O:11])[CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 88068Methyl 3-HydroxybenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 10932265Methyl 3-(allyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl-3-hydroxy-benzoate (1.09 g, 4.9 mmol), allyl bromide (0.73 g, 6.0 mmol) and potassium tert-butoxide (6.5 g, 5.8 mmol) in DMSO (15 mL) was stirred at room temperature for 16 hours. The mixture was poured into ice water, extracted with ether, washed with brine, dried (Na2SO4), and evaporated to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.55 (m, 1H), 7.45 (m, 2H), 7.24 (m, 1H), 6.12-5.98 (m, 1H), 5.44-5.26 (m, 2H), 4.64 (m, 2H), 3.84 (s, 3H).

Workup

  1. extractionextracted with ether
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-3700de60c54d442588ee07668f53c8f4
Source dataset
uspto-grants-2005_05
Patent number
US06887863B2

Reaction notes

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