O-Cresol → 1-(2-Bromoethoxy)-2-methylbenzene

HRID 271228ノート

反応式

HRID 271228 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[OH-].[Na+].[Br:11][CH:12](Br)[CH3:13].S([O-])(O)(=O)=O.C([NH3+])(C)(C)C>>[Br:11][CH2:12][CH2:13][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]

参加物

5

反応物 4

HCID 335O-CresolHCID 112011,1-DibromoethaneHCID 14798Sodium Hydroxide2 回HCID 24996679t-Butylammonium hydrogen sulfate

生成物 1

HCID 16225721-(2-Bromoethoxy)-2-methylbenzene

実験手順

2-Methyl-phenol (1 g, 9.25 mmol) in NaOH (aq) (3.24 mL, 12.96 mmol, 4M soln.) was treated with dibromoethane (2.74 mL, 31.7 mmol) and t-butylammoniumhydrogen sulfate (catalytic), and then placed in a Robbins™ oven at 99° C. for 72 hours. The pH was then adjusted to ˜8 with NaOH (4M aq. soln.) and the product extracted with CH2Cl2 (x3). The combined organic layer was washed with H2O (x2) and brine, dried over MgSO4. The resulting oil taken up in 4:1 hexane/EtOAc and passed through a plug of silica gel. The plug was then washed with 4:1 hexane/EtOAc and the filtrate concentrated to provide crude 2-bromo-1-(2-methylphenoxy)ethane.

後処理

  1. extractionthe product extracted with CH2Cl2 (x3)
  2. washThe combined organic layer was washed with H2O (x2) and brine
  3. dry with materialdried over MgSO4
  4. washThe plug was then washed with 4:1 hexane/EtOAc
  5. concentrationthe filtrate concentrated

出典と根拠

ORDレコード
ord-21e6a719f0544b869f90d556cdfe0898
出典データセット
uspto-grants-2008_11
特許番号
US07452889B2

反応ノート

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