Sulfuric Acid → HCID 58575472, compound

HRID 222198Notes

Reaction equation

HRID 222198 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14](O)[CH:15]([CH3:17])[CH3:16])=[CH:9][CH:8]=1>O>[Cl:6][C:7]1[CH:12]=[C:11]2[C:10]([CH2:13][CH2:14][C:15]2([CH3:17])[CH3:16])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 60797754HCID 60797754, compound

Product 1

HCID 58575472HCID 58575472, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated sulfuric acid (45.0 mL) was added to water (5.00 mL) carefully and allowed to cool down to room temperature. 1-(4-chlorophenyl)-3-methylbutan-2-ol (17.8 g, 0.0896 mol) was added portionwise over 30 minutes. After the addition, the mixture was left to stir at room temperature for 2 hours. The mixture was then poured onto ice and the aqueous layer was extracted with ether. The organic phase was washed water and then dried over magnesium sulphate and concentrated to yield crude product. The residue was purified by filtration through a plug of silica, eluting with dichloromethane, to yield the product, 12.6 g (78%). 1H-NMR (400 MHz, CDCl3, δ): 7.10 (m, 3H), 2.85 (t, J=7.2 Hz, 1H), 1.94 (t, J=7.2 Hz, 1H), 1.25 (s, 6H).

Workup

  1. additionAfter the addition
  2. waitthe mixture was left
  3. additionThe mixture was then poured onto ice
  4. extractionthe aqueous layer was extracted with ether
  5. washThe organic phase was washed water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. customto yield crude product
  9. filtrationThe residue was purified by filtration through a plug of silica
  10. washeluting with dichloromethane
  11. customto yield the product, 12.6 g (78%)

Sources & evidence

ORD record
ord-93c514130c784c1ebed70d99e4d05afa
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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