Chloromethyl Methyl Ether → HCID 12087966、化合物

HRID 2081076ノート

反応式

HRID 2081076 の反応式
C(N(CC)C(C)C)(C)C.[I:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:18])=[C:15]([OH:17])[CH:16]=1.Cl[CH2:20][O:21][CH3:22]>ClCCl.CCOCC>[I:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:18])=[C:15]([O:17][CH2:20][O:21][CH3:22])[CH:16]=1

参加物

6

反応物 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 114362355-Iodo-2-methylphenol

生成物 1

HCID 12087966HCID 12087966、化合物

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

N,N-Diisopropylethylamine (8.3 mL, 47.4 mmol) (Aldrich) was added to a suspension of 5-iodo-2-methyl-phenol (10.1 g, 43.1 mmol) (from Example 17 supra) in dichloromethane (40 mL) with cooling in an ice-water bath. Chloromethyl-methyl ether (6.5 mL, 86.1 mmol) (Aldrich) was added dropwise and the mixture stirred at room temperature for 5 hours. The mixture was then diluted with ether (200 mL) and washed with water (200 mL), followed by 0.1 N HCl (2×200 mL) and brine (200 mL). Aqueous layers were back washed with ether (200 mL). Organic solutions were combined, dried (MgSO4), filtered and concentrated. Residue was filtered through silica gel (Biotage 40 L) eluting with dichloromethane-hexenaes (1:4 V/v). Fractions were combined and concentrated to give 4-iodo-2-methoxymethoxy-1-methyl-benzene as colorless oil. (Yield 9.05 g, 75.6%).

後処理

  1. temperaturewith cooling in an ice-water bath
  2. washwashed with water (200 mL)
  3. washAqueous layers were back washed with ether (200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationResidue was filtered through silica gel (Biotage 40 L)
  8. washeluting with dichloromethane-hexenaes (1:4 V/v)
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-ccde8cd001784e27904b7e5943c03419
出典データセット
uspto-grants-2011_04
特許番号
US07932390B2

反応ノート

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