Hydrochloric Acid → 2-(4-t-Butylphenyl)-3-hydroxy-4-formylthiophene

HRID 1881532Notes

Reaction equation

HRID 1881532 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([CH:20]=[O:21])[C:15]=2[O:16]COC)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.O>O1CCOCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:12][CH:13]=[C:14]([CH:20]=[O:21])[C:15]=2[OH:16])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86604735HCID 86604735, compound

Product 1

HCID 860145662-(4-t-Butylphenyl)-3-hydroxy-4-formylthiopheneYield 69.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To 2-(4-t-butylphenyl)-3-methoxymethyloxy-4-formylthiophene (0.20 g, 0.66 mmol) in 1,4-dioxane (1.3 mL), 1 M hydrochloric acid (0.66 mL, 0.66 mmol) was added dropwise, and the reaction solution was stirred at 65° C. for 1 hour and at 80° C. for 1 hour. After addition of water, the reaction solution was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (chloroform) to give the desired product as a reddish brown oil (0.12 g, yield 68%).

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-631d193f2ffe424d8e4644ea12bb367a
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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