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

HRID 1602441Notes

Reaction equation

HRID 1602441 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 mixture was poured into water (3L) 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-d4e71159d67043fcaa7d3b75a9b81c6c
Source dataset
uspto-grants-1999_11
Patent number
US05981571

Reaction notes

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