4-Hydroxybenzoic Acid → 4-(4-Allyloxybutyloxy)benzoic acid

HRID 1982749ノート

反応式

HRID 1982749 の反応式
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH:8]=[CH2:9].[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:7]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)[CH:8]=[CH2:9]

参加物

6

反応物 4

HCID 1354-Hydroxybenzoic AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 137481731-Chloro-4-[(prop-2-en-1-yl)oxy]butane

生成物 1

HCID 219606264-(4-Allyloxybutyloxy)benzoic acid収率 123%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

A solution comprising 14 g of allyl (4-chlorobutyl) ether, 14 g of 4-hydroxybenzoic acid, 14 g of potassium carbonate and 50 ml of dimethylformamide was stirred at 90° C. for 3 hours. Water was added to it, and extracted with toluene, and the toluene layer was well washed with water, and toluene was evaporated away. 20 g of sodium hydroxide, 50 ml of water and 200 ml of ethanol were added to the resulting residue, and refluxed for 2 hours. Ethanol was evaporated away, and hydrochloric acid was added to make it acidic, and then extracted with diethyl ether and dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the resulting residue was recrystallized from a mixed solvent of ethanol and water to obtain 29 g of 4-(4-allyloxybutyloxy)benzoic acid.

後処理

  1. extractionextracted with toluene
  2. washthe toluene layer was well washed with water, and toluene
  3. customwas evaporated away
  4. addition20 g of sodium hydroxide, 50 ml of water and 200 ml of ethanol were added to the resulting residue
  5. temperaturerefluxed for 2 hours
  6. customEthanol was evaporated away
  7. additionhydrochloric acid was added
  8. extractionextracted with diethyl ether
  9. dry with materialdried with anhydrous magnesium sulfate
  10. customThe solvent was evaporated away
  11. customthe resulting residue was recrystallized from a mixed solvent of ethanol and water

出典と根拠

ORDレコード
ord-651364f736894c24b9436e1b8a8a9c0f
出典データセット
uspto-grants-2009_06
特許番号
US07541071B2

反応ノート

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