Ethylene Glycol → 3-Furancarboxylic acid, 5-butyl-4,5-dihydro-2-methyl-, ethyl ester

HRID 1029832

反応式

HRID 1029832 の反応式
C([CH:4]1[CH2:8][CH:7]([CH2:9][CH2:10][CH2:11][CH3:12])[O:6][C:5]1=[O:13])(=O)C.S([O-])(O)(=O)=O.[Na+].[CH2:20]([OH:23])[CH2:21]O.O1C=C[CH2:26][C:25]1=O.C(O)C>C1(C)C=CC(S(O)(=O)=O)=CC=1.[O-]CC.[Na+].O.C1CCCCC1>[CH2:9]([CH:7]1[CH2:8][C:4]([C:5]([O:6][CH2:25][CH3:26])=[O:13])=[C:20]([CH3:21])[O:23]1)[CH2:10][CH2:11][CH3:12]

参加物

10

反応物 5

HCID 174Ethylene Glycol2 回HCID 702EthanolHCID 1407652(3H)-FuranoneHCID 516919Sodium BisulfateHCID 108561723-Acetyl-5-butyloxolan-2-one

生成物 1

HCID 110529693-Furancarboxylic acid, 5-butyl-4,5-dihydro-2-methyl-, ethyl ester収率 63.5%

試薬・触媒・溶媒 4

HCID 6101p-Toluenesulfonic acid触媒HCID 2723922Sodium ethoxide触媒HCID 962Water溶媒2 回HCID 8078Cyclohexane溶媒2 回

反応条件

温度
71 °C

実験手順

A mixture containing 750 grams of 3-acetyl-5-butyl-dihydro-2 (3H)-furanone (4.0 mols), 750 grams of cyclohexane and 8.6 grams of sodium hydrogen sulfate were heated to reflux. To the refluxing mixture were added 250 grams of ethylene glycol (4.0 mols) over a period of 6 hours while the water formed by the reaction was collected in a Dean Stark Trap. An additional 110 grams of ethylene glycol (1.8 mols) was added over 22 hours to replace glycol carried over with the refluxing cyclohexane (azeotropic agent). After 36 hours, an analysis of the reaction mixture showed that the furanone was 95.4 percent converted to a ketal of the formula ##STR21## An aliquot of 94.5 grams of the mixture (0.22 mols) and 30.5 grams of anhydrous ethanol (0.66 mols) and 0.6 grams of p-toluene sulfonic acid were refluxed at 71° C. for 26 hours. The mixture was then neutralized with 0.73 grams of sodium ethoxide followed by stripping on a Rotovap under vacuum to a temperature of 90° C. The residue was water washed, dried on a Rotovap and distilled to provide 29.6 grams of 2-butyl-4-carbethoxy-5-methyl-2,3-dihydrofuran. The amount of recovered material represented a yield of 63.5 percent based on the amount of furanone reacted and a yield of 66.9% based on a 93.0% conversion of the ketal.

後処理

  1. temperaturewere heated to reflux
  2. customformed by the reaction
  3. customwas collected in a Dean Stark Trap
  4. customby stripping on a Rotovap under vacuum to a temperature of 90° C
  5. washwashed
  6. customdried on a Rotovap
  7. distillationdistilled

出典と根拠

ORDレコード
ord-9c09757cc1a34f5da767f36618e7bbf5
出典データセット
uspto-grants-1992_04
特許番号
US05103026

関連ノート

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