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

HRID 1854657ノート

反応式

HRID 1854657 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 117908852,6-Bis(methoxymethoxy)benzaldehyde収率 79%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-832f13be32294df28ba5e04cd428405b
出典データセット
uspto-grants-2015_02
特許番号
US08962674B2

反応ノート

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