Sulfuric Acid → 2-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-

HRID 363828Notes

Reaction equation

HRID 363828 reaction equation
[Al](OC(C)C)(OC(C)C)OC(C)C.S(=O)(=O)(O)O.CC(O)C.[CH3:23][C:24](=[CH:27][CH2:28][CH:29]1[CH2:33][CH:32]=[C:31]([CH3:34])[C:30]1([CH3:36])[CH3:35])[CH:25]=[O:26]>CC(C)=O>[CH3:23][C:24](=[CH:27][CH2:28][CH:29]1[CH2:33][CH:32]=[C:31]([CH3:34])[C:30]1([CH3:36])[CH3:35])[CH2:25][OH:26]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 30175572-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enalHCID 16685055Aluminum tri-iso-propoxide

Product 1

HCID 1198972-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-Yield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
85 °C

Procedure

10.2 g (50 mmol) of Al(O-i-Pr)3, 0.25g (2.5 mmol) of sulfuric acid and 180 g (3.0 mol) of IPA were fed into a 1000 ml four-necked round bottom flask under atmosphere of nitrogen, and stirred at 85° C., and then 192 g (1.0 mol) of 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-al was added. The reaction was conducted while fraction containing acetone generated at the solution temperature of 85° to 95° C. was removed by distillation. After 7 hours, the reaction solution was analyzed by GLC, 88% of 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol was obtained (corresponding to 92% selectivity for conversion of the aldehyde as the starting material).

Workup

  1. customgenerated at the solution temperature of 85° to 95° C.
  2. customwas removed by distillation

Sources & evidence

ORD record
ord-a8b69d3c19ed4602a7ee490ddb24ac2a
Source dataset
uspto-grants-1999_02
Patent number
US05874649

Reaction notes

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