Water → methyl 2-(prop-2-en-1-yloxy)benzoate

HRID 342083Notes

Reaction equation

HRID 342083 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[C:5]([O:14][CH3:15])(=[O:13])[C:6]1[C:7](=[CH:9][CH:10]=[CH:11][CH:12]=1)[OH:8].C(=O)([O-])[O-].[K+].[K+].O>C1COCC1.CN(C=O)C>[CH2:1]([O:8][C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[C:5]([O:14][CH3:15])=[O:13])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 962WaterHCID 4133Methyl SalicylateHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 221897methyl 2-(prop-2-en-1-yloxy)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of allyl bromide (152.4 g, 1.27 mol), methyl salicylate (162.44 g, 1.06 mol), and potassium carbonate (219.75 g, 1.59 mol) in THF (600 ml) and DMF (600 ml) was heated to reflux for 6 hr. The mixure was poured into water (3 L) and extracted with ethyl acetate three times. The ethyl acetate extracts were combined and washed with water and dried with brine. The ethyl acetate extracts were concentrated in vacuo to a yellow oil that was vacuum distilled to a clear oil (163.45 g, 80%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 hr
  3. extractionextracted with ethyl acetate three times
  4. washwashed with water
  5. dry with materialdried with brine
  6. concentrationThe ethyl acetate extracts were concentrated in vacuo to a yellow oil that
  7. distillationdistilled to a clear oil (163.45 g, 80%)

Sources & evidence

ORD record
ord-d4cb65fc2d2d407b84801ac0036d8c52
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

Loading…