Glycerol → 3-(4-Biphenylyl)-2-butenoic acid ethyl ester

HRID 1156272

反応式

HRID 1156272 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=O)[CH3:2].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[OH-].[NH4+].OCC(CO)O>O1CCCC1.B(OC)(OC)OC.[Zn]>[CH2:21]([O:20][C:18](=[O:19])[CH:17]=[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)[CH3:2])[CH3:22]

参加物

8

反応物 4

HCID 753GlycerolHCID 71134-AcetylbiphenylHCID 7748Ethyl bromoacetateHCID 14923Ammonium Hydroxide

生成物 1

HCID 545016723-(4-Biphenylyl)-2-butenoic acid ethyl ester

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒HCID 8470Trimethyl borate溶媒

実験手順

6.45 g (0.1 mole) of activated zinc metal (20 mesh) is placed in a flask fitted with a septum inlet and a magnetic stirrer. The system is maintained under a nitrogen atmosphere and kept at a temperature of 25° C. on a water bath. A solution of 19.6 g (0.1 mole) of 4-acetylbiphenyl in 75 ml of dry tetrahydrofuran and 75 ml of trimethyl borate (distilled from calcium hydride) is injected and the mixture stirred. 11.1 ml (0.1 mole) of freshly distilled ethyl bromoacetate is injected in one shot and the mixture stirred at 25° C. for 12 hours. A mixture of 25 ml of concentrated ammonium hydroxide and 75 ml of glycerine is added, and the aqueous phase is separated and extracted thrice with 25 ml portions of diethyl ether. The combined organic extracts are dried over anhydrous magnesium sulphate and the diethyl ether removed on a rotary evaporator; the residue is vacuum distilled and the fraction distilling at 0.125 mm at 171°-172° C. is collected. Recrystallisation from petroleum ether yields the heading compound.

後処理

  1. customfitted with a septum inlet and a magnetic stirrer
  2. temperatureThe system is maintained under a nitrogen atmosphere
  3. customkept at a temperature of 25° C. on a water bath
  4. stirringthe mixture stirred at 25° C. for 12 hours
  5. additionis added
  6. customthe aqueous phase is separated
  7. extractionextracted thrice with 25 ml portions of diethyl ether
  8. dry with materialThe combined organic extracts are dried over anhydrous magnesium sulphate
  9. customthe diethyl ether removed on a rotary evaporator
  10. distillationdistilled
  11. distillationthe fraction distilling at 0.125 mm at 171°-172° C.
  12. customis collected
  13. customRecrystallisation from petroleum ether
  14. customyields the heading compound

出典と根拠

ORDレコード
ord-2aa07ce1943c4955a100709333f3ec44
出典データセット
uspto-grants-1982_06
特許番号
US04335124

関連ノート

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