Acetic Acid → HCID 23442855, compound

HRID 2119724Notes

Reaction equation

HRID 2119724 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]([OH:14])=[CH:7][C:6]=1[CH:15]([CH3:17])[CH3:16])(=[O:3])[CH3:2].Cl[CH2:19][C:20]([CH3:22])=[CH2:21].C(O)(=O)C>ClCCl.[Cl-].[Zn+2].[Cl-]>[C:1]([O:4][C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]2[O:14][C:20]([CH3:22])([CH3:21])[CH2:19][C:7]=2[C:6]=1[CH:15]([CH3:17])[CH3:16])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 112413-Chloro-2-methyl-1-propeneHCID 14794455HCID 14794455, compound

Product 1

HCID 23442855HCID 23442855, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Under argon atmosphere, 294 mg of 4-acetoxy-3,5-diisopropylphenol was dissolved in 10 ml of anhydrous dichloromethane, 2.25 g of 3-chloro-2-methyl-1-propene, 202 mg of anhydrous zinc chloride and 0.5 ml of acetic acid were added, and the mixture was stirred at room temperature for 3 days. After the reaction was quenched with water, the reaction solution was extracted with hexane. The organic layers were washed with a saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 1% ethyl acetate) to give 316 mg of 5-acetoxy-2,2-dimethyl-4,6-diisopropyl-2,3-dihydrobenzofuran as a yellow oil (yield 88%).

Workup

  1. customAfter the reaction was quenched with water
  2. extractionthe reaction solution was extracted with hexane
  3. washThe organic layers were washed with a saturated aqueous sodium bicarbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 1% ethyl acetate)

Sources & evidence

ORD record
ord-a6e358a97c9f498e9473e77aaf0a910c
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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