1-Bromo-3-chloropropane → 2-(3-Chloropropoxy)-1,4-dimethoxybenzene

HRID 357431ノート

反応式

HRID 357431 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[OH:11].C([O-])([O-])=O.[K+].[K+].[Cl:18][CH2:19][CH2:20][CH2:21]Br>CC(C)=O>[Cl:18][CH2:19][CH2:20][CH2:21][O:11][C:4]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

参加物

5

反応物 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 53144982,5-Dimethoxyphenol

生成物 1

HCID 184672962-(3-Chloropropoxy)-1,4-dimethoxybenzene収率 86.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 2,5-dimethoxyphenol (29 g, 0.19 mol), K2CO3 (35 g), 3-chlorobromopropane (38.5 g, 0.25 mol) and acetone (250 ml) was stirred and refluxed for 6 hours, and then stirred at ambient temperature for 16 hours. The reaction was filtered, and the filtrate was concentrated to an orange liquid. The liquid was taken up into Et2O, and the organic layer washed with 1N NaOH, H2O, dried (MgSO4) and was concentrated to yield 37.8 g of an orange solid. An 11.7 g sample of this solid was flash chromatographed on silica gel (180 g) with 5% EtOAc/CH2Cl2 as eluent. Concentration of similar fractions gave 7.2 g of white, waxy solid, which was recrystallized from petroleum ether to afford a white solid, m.p. 48°-50° C.

後処理

  1. temperaturerefluxed for 6 hours
  2. stirringstirred at ambient temperature for 16 hours
  3. filtrationThe reaction was filtered
  4. concentrationthe filtrate was concentrated to an orange liquid
  5. washthe organic layer washed with 1N NaOH, H2O
  6. dry with materialdried (MgSO4)
  7. concentrationwas concentrated

出典と根拠

ORDレコード
ord-8e868150e3d84259bf0e73a057749c17
出典データセット
uspto-grants-1998_11
特許番号
US05840727

反応ノート

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