Chloromethyl Methyl Ether → 2,6-Bis(methoxymethoxy)benzaldehyde

HRID 1854657노트

반응식

HRID 1854657 반응식
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[CH:4]=[O:5].C(N(CC)C(C)C)(C)C.[CH3:20][O:21][CH2:22]Cl.[C:24]([O:27][CH2:28]C)(=O)C>ClCCl.CN(C)C1C=CN=CC=1.Cl>[CH3:20][O:21][CH2:22][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:24][O:27][CH3:28])[C:3]=1[CH:4]=[O:5]

참가 물질

8

반응물 4

HCID 7864Chloromethyl Methyl EtherHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 102858012,6-Dihydroxybenzaldehyde

생성물 1

HCID 117908852,6-Bis(methoxymethoxy)benzaldehyde수율 79%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매

실험 절차

2,6-Dihydroxybenzaldehyde (75 mg, 0.54 mmol) was placed in a 20 mL reaction vessel, and dissolved in 1.6 mL of dry dichloromethane. To the solution were added N,N-diisopropylethylamine (0.30 mL, 1.7 mmol), 4-dimethylaminopyridine (4 mg, 0.03 mmol), and chloromethyl methyl ether (103 μL, 0.68 mmol). After being stirred at room temperature overnight, the reaction mixture was diluted with 25 mL of ethyl acetate and 5 mL of 1N HCl, and extracted. The extract was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a pale yellow oil (96.9 mg, 79%).

후처리

  1. extractionextracted
  2. washThe extract was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-832f13be32294df28ba5e04cd428405b
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962674B2

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