Chloromethyl Methyl Ether → Methyl 2-(methoxymethoxy)-4-methylbenzoate

HRID 37011

反応式

HRID 37011 の反応式
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([OH:14])[C:7](=[CH:12][CH:13]=1)[C:8]([O:10][CH3:11])=[O:9].[CH3:15][O:16][CH2:17]Cl>CN(C)C=O.C(OCC)C>[CH3:15][O:16][CH2:17][O:14][C:6]1[CH:5]=[C:4]([CH3:3])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

参加物

6

反応物 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

生成物 1

HCID 13149247Methyl 2-(methoxymethoxy)-4-methylbenzoate収率 112.3%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of sodium hydride (1.62 g, 0.0675 mol) in 90 mL of dimethylformamide was added dropwise a solution of methyl 4-methylsalicylate (10.2 g, 0.0614 mol) in 20 mL of diethyl ether. After stirring for 15 minutes, a solution of chloromethyl methyl ether (5.6 mL, 0.0737 mol) in 10 mL of diethyl ether was added. The reaction mixture was stirred at room temperature for 18 hours and then it was partitioned between water and diethyl ether. The layers were separated and the aqueous layer was extracted an additional three times with diethyl ether. The combined organic extracts were washed with brine, dried with magnesium sulfate, and concentrated in vacuo to give 14.5 g of an oil. The product was purified by flash chromatography on silica gel eluting with 10%-15% ethyl acetate in hexane to give 9.41 g (73%) of product as an oil.

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 18 hours
  2. customit was partitioned between water and diethyl ether
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted an additional three times with diethyl ether
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a932d15aa55b4939965179150bfcc5eb
出典データセット
uspto-grants-1995_05
特許番号
US05418250

関連ノート

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