Sodium Iodide → 3-Hydroxy-4-propoxybenzaldehyde

HRID 2217071노트

반응식

HRID 2217071 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 219461763-Hydroxy-4-propoxybenzaldehyde수율 23.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6569Methyl Ethyl Ketone용매

실험 절차

Anhydrous potassium carbonate (5.9 g, 0.043 mmol) and sodium iodide (0.434 g, 4.3 mmol) were added to 3,4-dihydroxybenzaldehyde (4.0 g, 28.9 mmol), in butanone (100 ml), at room temperature. The reaction was stirred for 10 min after which propyl bromide (2.628 ml, 28.9 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 (3×50 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 1.21 g (23.3%) of 3-hydroxy-4-propoxybenzaldehyde as an off-white solid.

후처리

  1. additionwas added dropwise
  2. temperaturethe reaction was refluxed for 3 h
  3. extractionthe product was extracted with dichloromethane (3×50 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)

출처 및 근거

ORD 기록
ord-da14e69926e54c4ca280e7d37e8537b6
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07112698B2

반응 노트

불러오는 중…