Hydrochloric Acid → Methyl 2-methoxymethoxy-3-n-propyl-4-methoxybenzoate

HRID 465911ノート

反応式

HRID 465911 の反応式
[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]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 10967Bis(Chloromethyl) EtherHCID 5462222PotassiumHCID 14719500Methyl 2-hydroxy-3-n-propyl-4-methoxybenzoate

生成物 1

HCID 14719501Methyl 2-methoxymethoxy-3-n-propyl-4-methoxybenzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  1. stirringthe mixture was agitated at 0° C. for 50 minutes
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in evacuated atomosphere

出典と根拠

ORDレコード
ord-21b4791723c5442387e74ec4867f2f03
出典データセット
uspto-grants-1992_10
特許番号
US05155106

反応ノート

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