Aluminum(III) Chloride → HCID 60026719, compound

HRID 400635Notes

Reaction equation

HRID 400635 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12](=[O:17])[CH:13]=[C:14]([CH3:16])[CH3:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[C:1]([C:5]1[CH:6]=[C:7]2[C:8](=[CH:9][CH:10]=1)[O:11][C:12](=[O:17])[CH2:13][C:14]2([CH3:16])[CH3:15])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 60026695HCID 60026695, compound

Product 1

HCID 60026719HCID 60026719, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 3-methylbut-2-enoic acid 4-tert-butylphenyl ester (23 g, 99 mmol) in 50 mL of carbon disulfide (CS2) was added 19.8 g of aluminum chloride (AlCl3) portionwise over the course of 1 hour, a very exothermic reaction. After stirring for several hours, TLC showed the reaction was complete. The reaction mixture was concentrated under a stream of nitrogen gas, and the residue poured over ice and extracted with ethyl acetate. The organics were combined, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified on silica pad (0% to 5% ethyl acetate-hexanes) to give 8.1 g of 6-tert-butyl-4,4-dimethylchroman-2-one as an oil.

Workup

  1. customa very exothermic reaction
  2. concentrationThe reaction mixture was concentrated under a stream of nitrogen gas
  3. additionthe residue poured over ice
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica pad (0% to 5% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-6d654c48b870419dbb19cdf98e70ba93
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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