Sodium Iodide → 3-Hydroxy-4-propoxybenzaldehyde

HRID 2217062ノート

反応式

HRID 2217062 の反応式
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[OH:18])[CH:13]=[O:14].[CH2:19](Br)[CH2:20][CH3:21]>CC(=O)CC.O>[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][CH3:21])[CH:13]=[O:14]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 78401-BromopropaneHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate

生成物 1

HCID 219461763-Hydroxy-4-propoxybenzaldehyde収率 22%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

Anhydrous potassium carbonate (1.5 g, 10.8 mmol) and sodium iodide (0.108 g, 0.72 mmol) were added to 3,4-dihydroxybenzaldehyde (1.0 g, 7.2 mmol), in butanone (50 ml), at room temperature. The reaction was stirred for 10 min after which propyl bromide (0.657 ml, 7.2 mmol) was added dropwise and the reaction was refluxed for 3 h. The reaction mixture was diluted with water and the product was extracted with dichloromethane (3×25 ml), the combined organic layers were dried over magnesium sulphate and reduced in vacuo. Purification by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate) afforded 0.248 g (22%) of 3-hydroxy-4-propoxybenzaldehyde as an off-white solid.

後処理

  1. additionwas added dropwise
  2. temperaturethe reaction was refluxed for 3 h
  3. extractionthe product was extracted with dichloromethane (3×25 ml)
  4. dry with materialthe combined organic layers were dried over magnesium sulphate
  5. customPurification by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate)

出典と根拠

ORDレコード
ord-578e6df33a8f42a788a0800f5c30b230
出典データセット
uspto-grants-2006_09
特許番号
US07112698B2

反応ノート

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