Water → Methyl 3-methoxymethoxy-2-naphthoate

HRID 862065

反応式

HRID 862065 の反応式
[OH:1][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Na+].[CH3:18][O:19][CH2:20]Cl.O>C1COCC1>[CH3:18][O:19][CH2:20][O:1][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

参加物

6

反応物 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 70163Methyl 3-hydroxy-2-naphthoate

生成物 1

HCID 53900226Methyl 3-methoxymethoxy-2-naphthoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of methyl 3-hydroxy-2-naphthoate (7.01 g) in THF (200 ml) was cooled to 0° C., to which was added 60% sodium hydride (1.58 g) during 10 minutes. Then, the mixture was stirred for one hour at room temperature, to which was added dropwise chloromethyl methyl ether (2.8 ml). The mixture was then stirred for two hours, to which was added water to quench the reaction, followed by extraction with ethyl acetate. The organic layer was dried (anhydrous magnesium sulfate), and distilled off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give methyl 3-methoxymethoxy-2-naphthoate (7.11 g) (Compound B-19). The physical properties are shown in Table 7.

後処理

  1. stirringThe mixture was then stirred for two hours, to which
  2. customto quench
  3. customthe reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  6. distillationdistilled off the solvent under reduced pressure
  7. customThe residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-41bd6cd5a004418aa0a9fd034ac769b7
出典データセット
uspto-grants-1998_02
特許番号
US05716971

関連ノート

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