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

HRID 130269ノート

反応式

HRID 130269 の反応式
CN(C)C=O.[CH2:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13]Cl)[CH:7]=[CH2:8].[OH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)[CH:7]=[CH2:8]

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

実験手順

A dimethylformamide (50 ml) solution of allyl(4-chlorobutyl) ether 14 g, 4-hydroxybenzoic acid 14 g and potassium carbonate 14 g was stirred at 90° C. for 3 hours. Water was added thereto, and the solution was extracted with toluene. The toluene layer was washed well with water, and then toluene was distilled off. Sodium hydroxide 20 g, water 50 ml and ethanol 200 ml were added to the resulting residue and refluxed for 2 hours. Ethanol was distilled off, and then hydrochloric acid was added to the residue to acidify the solution. The solution was extracted with diethyl ether, and the extract was dried on anhydrous magnesium sulfate. A residue obtained by distilling the solvent off was recrystallized from a mixed solvent of ethanol and water to obtain 29 g of 4-(4-allyloxybutyloxy)benzoic acid. Phase transition temperature: C94N107I.

後処理

  1. extractionthe solution was extracted with toluene
  2. washThe toluene layer was washed well with water
  3. distillationtoluene was distilled off
  4. additionSodium hydroxide 20 g, water 50 ml and ethanol 200 ml were added to the resulting residue
  5. temperaturerefluxed for 2 hours
  6. distillationEthanol was distilled off
  7. additionhydrochloric acid was added to the residue
  8. extractionThe solution was extracted with diethyl ether
  9. dry with materialthe extract was dried on anhydrous magnesium sulfate
  10. customA residue obtained
  11. distillationby distilling the solvent
  12. customoff was recrystallized from a mixed solvent of ethanol and water

出典と根拠

ORDレコード
ord-c4e2dfceb9af48f38c8dce42e18a34a7
出典データセット
uspto-grants-2008_06
特許番号
US07381350B2

反応ノート

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