Water → 4-Methoxy-3-(3-methoxypropoxy)benzenemethanol

HRID 2258291ノート

反応式

HRID 2258291 の反応式
[CH3:1][O-:2].[Na+].[CH3:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[O:14][CH2:15][CH2:16][CH2:17]Br.O>CO>[CH3:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][C:7]=1[O:14][CH2:15][CH2:16][CH2:17][O:2][CH3:1]

参加物

5

反応物 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 229246273-(3-Bromopropoxy)-4-methoxybenzaldehyde

生成物 1

HCID 451081634-Methoxy-3-(3-methoxypropoxy)benzenemethanol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A 30% solution of sodium methanolate in methanol (0.86 liter, 4.64 mol) is added dropwise at 61°-64° C. to a solution of 4-methoxy-3-(3-bromopropoxy)-benzaldehyde (844 g) in methanol (4.15 liters). The batch is stirred under reflux for a further 1.5 hours, then allowed to cool to room temperature, and water (150 ml) is added. The methanol is removed in a rotary evaporator (30° C. bath temperature) and the residue is then partitioned between diethyl ether (3×3 liters) and ice-cold 4N hydrochloric acid. The combined organic phases are washed with water and saturated sodium hydrogen carbonate solution, dried over magnesium sulfate and concentrated. The residue is purified by FC on silica gel (ethyl acetate/hexane 1:3) and the title compound is obtained in the form of an oil (498 g): Rf (ethyl acetate/hexane 1:2)=0.18.

後処理

  1. temperatureunder reflux for a further 1.5 hours
  2. customThe methanol is removed in a rotary evaporator (30° C. bath temperature)
  3. customthe residue is then partitioned between diethyl ether (3×3 liters) and ice-cold 4N hydrochloric acid
  4. washThe combined organic phases are washed with water and saturated sodium hydrogen carbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue is purified by FC on silica gel (ethyl acetate/hexane 1:3)

出典と根拠

ORDレコード
ord-79d255df8f7a4743b7d172888776455a
出典データセット
uspto-grants-1997_08
特許番号
US05659065

反応ノート

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