Aluminum isopropoxide → HCID 20163297, compound

HRID 246893Notes

Reaction equation

HRID 246893 reaction equation
CC([O-])C.CC([O-])C.CC([O-])C.[Al+3].[CH3:14][C:15]1([C:23](=[O:25])[CH3:24])[CH:20]([CH3:21])[CH2:19][C:18]([CH3:22])=[CH:17][CH2:16]1.C(O)(C)C.CC(C)=O>C(O)(C)C>[CH3:14][C:15]1([CH:23]([OH:25])[CH3:24])[CH:20]([CH3:21])[CH2:19][C:18]([CH3:22])=[CH:17][CH2:16]1

Participants

5

Reactant 3

HCID 11143Aluminum isopropoxideHCID 201632901-(1,4,6-Trimethylcyclohex-3-en-1-yl)ethan-1-oneHCID 22386392HCID 22386392, compound

Product 1

HCID 20163297HCID 20163297, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 0.33 moles (68 g) aluminum isopropylate in 600 ml isopropanol was heated to boiling in a 1-liter 3-necked flask with a magnetic stirrer, packed column, dropping funnel and thermometer. Within two hours 1 mole (166 g) 1-(1,4,6-trimethylcyclohex-3-en-1-yl)ethan-1-one (as per Example 1) was added dropwise to the boiling solution, and at the same time the isopropanol/acetone mixture formed was distilled off. After 10 hours the reaction was ended (after no more acetone could be detected in the distillate). Thereupon isopropanol still remaining was drawn off, and 175 ml 20% by weight hydrochloric acid was added to the residue after cooling. Extraction was carried out and the organic phase was washed free of acid. After fractional distillation 151 g of the desired end product was obtained, corresponding to 90% of the theoretical amount.

Workup

  1. customto boiling in a 1-liter 3-necked flask with a magnetic stirrer
  2. distillationwas distilled off
  3. addition175 ml 20% by weight hydrochloric acid was added to the residue
  4. temperatureafter cooling
  5. extractionExtraction
  6. washthe organic phase was washed free of acid
  7. distillationAfter fractional distillation 151 g of the desired end product
  8. customwas obtained, corresponding to 90% of the theoretical amount

Sources & evidence

ORD record
ord-b05917b696c74f1cb3a503a93e53c71c
Source dataset
uspto-grants-1987_11
Patent number
US04704477

Reaction notes

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