Acetic Acid → 1,3-Dihydro-1-oxoisobenzofuran-5-carboxylic acid

HRID 48536

反応式

HRID 48536 の反応式
OS(O)(=O)=O.O=S(=O)=O.[C:10]([OH:21])(=[O:20])[C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.O1COCO[CH2:23]1.C(O)(=O)C>O>[C:15]([C:14]1[CH:18]=[C:19]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:21])[O:20][CH2:23]2)([OH:17])=[O:16]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 7489Terephthalic AcidHCID 80811,3,5-TrioxaneHCID 24681Fuming sulfuric acid

生成物 1

HCID 785171,3-Dihydro-1-oxoisobenzofuran-5-carboxylic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
131.5 °C

実験手順

In a 3000-l glass lined reactor, 550 Kg of oleum containing 25% of SO3 are charged under vacuum and good aspiration, then, consecutively, under stirring, 56 Kg of terephthalic acid at 20-23° C. and 26 Kg of 1,3,5-trioxane at 15-20° C. are added thereinto. The reactor is heated at 130-133° C. for 4 hours, then the mixture is cooled to 20-23° C. and 118 Kg of glacial acetic acid are couled portionwise thereinto at a temperature not higher than 25° C. At the end of this operation, 1000 Kg of water are added portionwise, whereby the temperature is maintained not higher than 43-45° C. by circulation of water in the jacket. The mixture is stirred for about 1 hour at 20-23° C., then the product is centrifugated, squeezed and abundantly washed with water in order to remove the larger amount of sulfuric acid from the mother liquors and to obtain 100-105 Kg of 5-carboxyphthalide as a well squeezed, wet raw-product. In a 3000-l stainless steel reactor the product thus obtained is suspended in 680 Kg of deionized water and a solution of 60 Kg of sodium bicarbonate in 540 Kg of deionized water is then slowly added to said suspension to a pH of 7.0-7.2. To the solution thus obtained, lightly cloudy, 10 Kg of Celite® are added, the solid is filtered off and the solution, at a temperature of 22-25° C., is brought to pH=3 with 32% hydrochloric acid, then stirred at 20-22° C. and centrifugated. The product is well squeezed, abundantly washed with deionized water and dried under vacuum to give 41-43.7 Kg of 5-carboxyphthalide.

後処理

  1. temperaturethe mixture is cooled to 20-23° C.
  2. customhigher than 25° C
  3. stirringThe mixture is stirred for about 1 hour at 20-23° C.
  4. washabundantly washed with water in order
  5. customto remove the larger amount of sulfuric acid from the mother liquors

出典と根拠

ORDレコード
ord-5b78dd2d437545e59bc03a3497c9ccc2
出典データセット
uspto-grants-2004_03
特許番号
US06703516B2

関連ノート

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