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

HRID 37011노트

반응식

HRID 37011 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 13149247Methyl 2-(methoxymethoxy)-4-methylbenzoate수율 112.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a932d15aa55b4939965179150bfcc5eb
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05418250

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