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

HRID 363827

Reaction equation

HRID 363827 reaction equation
[Al](OC(C)C)(OC(C)C)OC(C)C.[CH3:14][C:15](=[CH:18][CH2:19][CH:20]1[CH2:24][CH:23]=[C:22]([CH3:25])[C:21]1([CH3:27])[CH3:26])[CH:16]=[O:17].ClC(Cl)(Cl)C(O)=O.C(O)(C)C>CC(C)=O.C1(C)C=CC=CC=1>[CH3:14][C:15](=[CH:18][CH2:19][CH:20]1[CH2:24][CH:23]=[C:22]([CH3:25])[C:21]1([CH3:27])[CH3:26])[CH2:16][OH:17]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 6421Trichloroacetic AcidHCID 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 81%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

3.07 g (15 mmol) of Al(O-i-Pr)3 and 30 ml of toluene were fed into a 100 ml four-necked round bottom flask under atmosphere of nitrogen, and stirred at room temperature, and then 28.8 g (150 mmol) of 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-al, then 0.25 g (1.5 mmol) of trichloroacetic acid, and further 18.0 g (300 mmol) of isopropyl alcohol were added while stirring at room temperature. Reaction was conducted while fraction containing acetone generated at the solution temperature of 80° to 92° C. was distilled off. After 6 hours, the reaction solution was analyzed by GLC, 81% of 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol was obtained (corresponding to 90% selectivity for conversion of the aldehyde as the starting material).

Workup

  1. stirringwhile stirring at room temperature
  2. customReaction
  3. customgenerated at the solution temperature of 80° to 92° C.
  4. distillationwas distilled off

Sources & evidence

ORD record
ord-3c69ea5d177245898c506b4aba8756cd
Source dataset
uspto-grants-1999_02
Patent number
US05874649

Linked notes

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