Hydrochloric Acid → HCID 23442895, compound

HRID 2119726Notes

Reaction equation

HRID 2119726 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12]C(=O)C)=[CH:7][C:6]=1[C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:3])[CH3:2].S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[Na+].Cl>C(O)C.O>[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[CH:7][C:6]=1[C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 23442875HCID 23442875, compound

Product 1

HCID 23442895HCID 23442895, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

1.05 g of 1,4-diacetoxy-2-t-butyl-6-methylbenzene was dissolved in 10 ml of ethanol and 2 ml of an aqueous solution containing 0.23 g of sodium hydrosulfite and 0.17 g of sodium hydroxide was added dropwise with stirring at 0° C. The reaction solution was neutralized with 1N hydrochloric acid, and then combined with water and extracted with ethyl acetate. The organic layers were dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 10% ethyl acetate) to give 0.44 g of 4-acetoxy-3-t-butyl-5-methylphenol as a pale yellow oil (yield 50%).

Workup

  1. additionwas added dropwise
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 10% ethyl acetate)

Sources & evidence

ORD record
ord-6d58428c85f84707be02277a1a4a3ff7
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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