Hydrochloric Acid → Methyl 2-methoxymethoxy-3-n-propyl-4-methoxybenzoate
Reaction equation
[K].[OH:2][C:3]1[C:12]([CH2:13][CH2:14][CH3:15])=[C:11]([O:16][CH3:17])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].Cl[CH2:19][O:20][CH2:21]Cl.Cl>O1CCCC1>[CH3:19][O:20][CH2:21][O:2][C:3]1[C:12]([CH2:13][CH2:14][CH3:15])=[C:11]([O:16][CH3:17])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]Participants
Procedure
In argon atmosphere, a solution of potassium t-buthoxide (18.7 g) in tetrahydrofuran (200 ml) was cooled to 0° C., and to this solution was added dropwise a solution of methyl 2-hydroxy-3-n-propyl-4-methoxybenzoate (28 g) in tetrahydrofuran (100 ml) in 10 minutes, and the mixture was agitated for another 20 minutes. Chloromethyl ether (19.0 ml) was added thereto, and the mixture was agitated at 0° C. for 50 minutes. The reaction mixture was poured into 1N aqueous hydrochloric acid, and extracted twice with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, and then concentrated in evacuated atomosphere. The residue was subjected to column chromatography using silica gel, and there was obtained methyl 2-methoxymethoxy-3-n-propyl-4-methoxybenzoate (29.9 g) from fractions eluted with n-hexane-ethyl acetate (10:1 to 5:1).
Workup
- stirringthe mixture was agitated at 0° C. for 50 minutes
- extractionextracted twice with ethyl acetate
- washThe organic layer was washed with saturated sodium bicarbonate
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in evacuated atomosphere
Sources & evidence
- ORD record
- ord-21b4791723c5442387e74ec4867f2f03
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05155106
Reaction notes
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