Sulfuric Acid → HCID 22770570, compound

HRID 1834705Notes

Reaction equation

HRID 1834705 reaction equation
C(OC[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11]C=1)=[CH2:8])(=O)C.S(=O)(=O)(O)O.C(OCCC(C1C=CC=CC=1)=C)(=[O:22])C.S(=O)(=O)(O)O.[OH-].[Na+].[CH2:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1>>[CH:7]([CH:9]1[CH2:14][CH:13]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:12]=[CH:11][O:22]1)([CH3:6])[CH3:8]

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 8078CyclohexaneHCID 14798Sodium HydroxideHCID 817393-Phenylbut-3-enyl acetateHCID 20306567HCID 20306567, compound

Product 1

HCID 22770570HCID 22770570, compound

Procedure

In a 500 ml three neck reaction flask equipped with stirrer, thermometer, reflux condenser and addition funnel is placed 72 gms (1 mole) of iosbutyl aldehyde. The isobutyl aldehyde is heated to 66° C (reflux) and from the additional funnel, over a period of 1 hour, is added a mixture of 204 g (1 mole) of 3-phenyl-3-buten-1-yl acetate and 1 g concentrated sulfuric acid. During addition of the 3-phenyl-3-buten-1-yl acetate/sulfuric acid mixture, the reaction mass temperature increases to 80°-85° C. At the end of the addition of the mixture, the reaction mass is stirred for a period of three hours at 80°-85° C. The reaction mass is then cooled to room temperature and 100 ml of a 10% aqueous sodium hydroxide solution is added thereto with stirring, followed by 100 ml cyclohexane. The resulting mixture is transferred to a separatory funnel and the aqueous layer is removed. The organic layer is then washed with one 100 ml portion of 10% aqueous sodium chloride. The organic layer is then stripped of solvent and rushed over. To the rushed over material 4.5 gms Primol®, 0.5 gms triethanolamine and 0.1 gms of Ionox® is added. The resulting material is then distilled in a 8 plate vigreux column yielding the following fractions:

Workup

  1. temperaturethermometer, reflux
  2. additioncondenser and addition funnel
  3. temperature(reflux)
  4. additionis added
  5. temperaturethe reaction mass temperature increases to 80°-85° C
  6. additionAt the end of the addition of the mixture
  7. stirringwith stirring
  8. customThe resulting mixture is transferred to a separatory funnel
  9. customthe aqueous layer is removed
  10. washThe organic layer is then washed with one 100 ml portion of 10% aqueous sodium chloride
  11. additionis added
  12. distillationThe resulting material is then distilled in a 8 plate vigreux column
  13. customyielding the following fractions

Sources & evidence

ORD record
ord-f330e6bd114e451cb180faa2911035d9
Source dataset
uspto-grants-1978_01
Patent number
US04071034

Reaction notes

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