Hydrochloric Acid → Methyl 2-allyloxy-3-formyl-4-methoxybenzoate

HRID 1241243Notes

Reaction equation

HRID 1241243 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[OH-].[K+].[OH:7][C:8]1[C:17]([CH:18]=[O:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].Cl>CS(C)=O>[CH2:1]([O:7][C:8]1[C:17]([CH:18]=[O:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 219335993-Formyl-2-hydroxy-4-methoxy-benzoic acid methyl ester

Product 1

HCID 21933587Methyl 2-allyloxy-3-formyl-4-methoxybenzoateYield 36%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

At room temperature, 23.2 g (0.192 mol) of allyl bromide were added dropwise to a mixture of 21.0 g (0.375 mol) of potassium hydroxide and 20.2 g (0.096 mol) of methyl 2-hydroxy-3-formyl-4-methoxybenzoate in 500 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature for 4 hours. The mixture was subsequently stirred into 1.5 l of 3% strength aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic phases were washed with water and dried, and the solvent was removed. Silica gel chromatography using cyclohexane/ethyl acetate=1:2 gave 7.7 g (36%) of methyl 2-allyloxy-3-formyl-4-methoxybenzoate in the form of a yellowish oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with water
  3. customdried
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-169f1178365149fb86f98932f7f04ab5
Source dataset
uspto-grants-2006_10
Patent number
US07115545B1

Reaction notes

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