Sodium Hydroxide → HCID 12094379, compound

HRID 2119722Notes

Reaction equation

HRID 2119722 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]([OH:14])=[C:7]([CH:15](O)[CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:6]=1[CH:22]([CH3:24])[CH3:23])(=[O:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([O:4][C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]2[O:14][C:16]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][C:7]=2[C:6]=1[CH:22]([CH3:24])[CH3:23])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 23442887HCID 23442887, compound

Product 1

HCID 12094379HCID 12094379, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.51 g of 4-acetoxy-2-(2-ethyl-1-hydroxybutyl)-3,5-diisopropylphenol dissolved in 10 ml of toluene, 0.58 g of p-toluenesulfonic acid monohydrate was added, and the mixture was heated under reflux for 1.5 hours. The reaction mixture was combined with a 2N aqueous sodium hydroxide solution and extracted with hexane. The organic layers were washed with 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 433 mg of 5-acetoxy-2,2-diethyl-4,6-diisopropyl-2,3-dihydrobenzofuran as a yellow oil (yield 90%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. extractionextracted with hexane
  4. washThe organic layers were washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 1% ethyl acetate)

Sources & evidence

ORD record
ord-afdaba64a4654c6098f7112b53b5be95
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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