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

HRID 48535

反応式

HRID 48535 の反応式
S(=O)(=O)(O)O.[C:6]([OH:17])(=[O:16])[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.O1COCO[CH2:19]1>O>[C:11]([C:10]1[CH:14]=[C:15]2[C:7](=[CH:8][CH:9]=1)[C:6](=[O:17])[O:16][CH2:19]2)([OH:13])=[O:12]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 7489Terephthalic AcidHCID 80811,3,5-Trioxane

生成物 1

HCID 785171,3-Dihydro-1-oxoisobenzofuran-5-carboxylic acid収率 104.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
1 °C

実験手順

To 153 ml of fuming sulfuric acid, containing 25% of SO3, 50 g (0.3 m) of terephthalic acid are added, in small portions, at 20-22° C., then to the mixture thus obtained 23 g (0.25 m) of 1,3,5-trioxane are added portionwise thereinto. The mixture is kept about 30 minutes under stirring, without cooling, then the temperature is brought to 135-140° C. and heating is continued for 2-2.5 hours, whereby the reaction is complete, as shown by a HPLC control. The reaction mixture is cooled to 0-2° C. and 1000 ml of cold water are added thereto without exceeding 20-23° C., by keeping in mind that, during the addition of the first 15-20 ml of water, exothermia occurs, whilst afterwards the temperature may be easily controlled. The mixture is kept 1 hour under stirring at 20-25° C., the product thus obtained is filtered, still moist triturated in 300 ml of water repeatedly until the reddish colour of the mother liquors disappears. After the third trituration, the pH of the mother liquors stabilizes at values ranging from 5 to 6. The product is dried in vacuo at 45-50° C. until constant weight to give 47.5 g of 5-carboxyphthalide with a titer and a purity (HPLC)>95%.

後処理

  1. additionare added, in small portions, at 20-22° C.
  2. temperaturewithout cooling
  3. customis brought to 135-140° C.
  4. temperatureheating
  5. waitis continued for 2-2.5 hours
  6. customwithout exceeding 20-23° C.
  7. waitThe mixture is kept 1 hour
  8. stirringunder stirring at 20-25° C.
  9. customthe product thus obtained
  10. filtrationis filtered
  11. customstill moist triturated in 300 ml of water repeatedly until the reddish colour of the mother liquors
  12. customThe product is dried in vacuo at 45-50° C. until constant weight

出典と根拠

ORDレコード
ord-221882ef031c4f25886cd074b5e658ba
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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