Ethylparaben → 4-(4-Hydroxybutoxy)benzoic acid

HRID 2229988

反応式

HRID 2229988 の反応式
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8]Cl)(=O)C.[OH:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[I-].[K+]>[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:20][CH:21]=1

参加物

6

反応物 3

HCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 233991-Butanol, 4-chloro-, 1-acetate

生成物 1

HCID 152185964-(4-Hydroxybutoxy)benzoic acid収率 89.5%

試薬・触媒・溶媒 2

HCID 4875Potassium Iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

276.6 g of 4-chlorobutyl acetate (1.8 mol) were added to a solution of 249 g of ethyl 4-hydroxybenzoate (1.5 mol), 3 g of potassium iodide (0.018 mol) and 248 g of potassium carbonate (1.8 mol) in 2 l of DMF, and the mixture was stirred at 90° C. for 11 hours. The reaction mixture was poured into 5 l of ice-water, and the precipitate was filtered off with suction and washed with 4 l of ice-water. The crude product was dissolved in 3 l of ethanol, potassium hydroxide (400 g) was added, and the mixture was refluxed for 3 hours. The reaction mixture was poured into 6 l of ice-water and acidified using concentrated hydrochloric acid, and the precipitate was filtered off. The precipitate was washed with water until neutral and then dried, giving 282.1 g of 4-(4′-hydroxybutoxy)benzoic acid (yield 89%). b) A solution of 282 g of 4-(4′-hydroxybutoxy)benzoic acid (1.34 mol), 230 ml of freshly distilled acrylic acid (3.35 mol), 0.3 g of 2,6-di-tert-butyl-4-(dimethylaminomethylene)phenol (Ethanox® 703) and 23.7 g of p-toluenesulfonic acid in 1.1 liter of 1,1,1-trichloroethane was refluxed for 10 hours on a water separator. The reaction mixture was cooled to 60° C.-70° C. and stirred into 2.5 l of petroleum ether, and the precipitate was filtered off. After washing with petroleum ether, the precipitate was dried for 24 hours at room temperature under reduced pressure, giving 223.7 g of 4-(4′-acryloxybutoxy)benzoic acid (yield 60%).

後処理

  1. filtrationthe precipitate was filtered off with suction
  2. washwashed with 4 l of ice-water
  3. dissolutionThe crude product was dissolved in 3 l of ethanol
  4. additionpotassium hydroxide (400 g) was added
  5. temperaturethe mixture was refluxed for 3 hours
  6. additionThe reaction mixture was poured into 6 l of ice-water
  7. filtrationthe precipitate was filtered off
  8. washThe precipitate was washed with water until neutral and
  9. customthen dried

出典と根拠

ORDレコード
ord-f48699e7a4974519b82c87b8cfb1f715
出典データセット
uspto-grants-2002_07
特許番号
US06423246B1

関連ノート

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