Sulfuric Acid → HCID 90021602, compound

HRID 1486135Notes

Reaction equation

HRID 1486135 reaction equation
[C:1](O)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[OH:31])([CH2:23][CH3:24])[CH3:22].S(=O)(=O)(O)O>C(O)(=O)C>[CH:21]([C:25]1[CH:30]=[C:29]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:28]=[CH:27][C:26]=1[OH:31])([CH2:23][CH3:24])[CH3:22]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6457TriphenylcarbinolHCID 69842-sec-Butylphenol

Product 1

HCID 90021602HCID 90021602, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 250 mL 1-neck flask was equipped with a magnetic stirrer and a reflux condenser with nitrogen blanket. The flask was charged with 6.52 grams (0.025 moles) of trityl alcohol, 3.77 grams (0.025 moles) of o-sec-butylphenol, and 50 mL of glacial acetic acid. The mixture was stirred under nitrogen at room temperature to give a clear, yellow solution. Concentrated sulfuric acid (5 mL) was then added in one portion. The solution immediately became dark red-brown. The solution was stirred at room temperature for 2 days, during which time solids separated out. The reaction mixture was filtered, and the solids were washed on the filter with several portions of water. After drying in a vacuum oven at 65° C. for 3 hours, the yield of product was 7.34 grams (75% yield). MP=135-136° C. GPC analysis showed a purity of >99%. The structure was confirmed by IR, 1H- and 13C-NMR analyses.

Workup

  1. customA 250 mL 1-neck flask was equipped with a magnetic stirrer and a reflux condenser with nitrogen blanket
  2. customto give a clear, yellow solution
  3. stirringThe solution was stirred at room temperature for 2 days, during which time solids
  4. customseparated out
  5. filtrationThe reaction mixture was filtered
  6. washthe solids were washed on the
  7. filtrationfilter with several portions of water
  8. customAfter drying in a vacuum oven at 65° C. for 3 hours

Sources & evidence

ORD record
ord-bb647d37360c49438bf4d08f91a663fa
Source dataset
uspto-grants-2016_08
Patent number
US09422493B2

Reaction notes

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