Water → HCID 58575472, compound

HRID 447656Notes

Reaction equation

HRID 447656 reaction equation
S(=O)(=O)(O)O.O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15](O)[CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1>>[Cl:7][C:8]1[CH:13]=[C:12]2[C:11]([CH2:14][CH2:15][C:16]2([CH3:18])[CH3:17])=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric Acid2×HCID 60797754HCID 60797754, compound

Product 1

HCID 58575472HCID 58575472, compoundYield 63%

Procedure

To a solution of concentrated sulfuric acid (3.00 mL, 0.056 mol) in water (0.28 mL, 0.0156 mol) was added 1-(4-chlorophenyl)-3-methylbutan-2-ol (1.00 g, 0.00503 mol) over 30 minutes. Additional sulfuric acid was added to dissolve the solid. The mixture was stirred for 2 hours. The mixture was poured onto ice then extracted with ether. The organic phase was washed (water), dried (MgSO4), filtered, and concentrated. The residue was filtered through a plug of silica with CH2Cl2 to afford the title compound (0.568 g, 63%).

Workup

  1. dissolutionto dissolve the solid
  2. additionThe mixture was poured onto ice
  3. extractionthen extracted with ether
  4. washThe organic phase was washed (water)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationThe residue was filtered through a plug of silica with CH2Cl2

Sources & evidence

ORD record
ord-87b96ebf5ee34c6a9d7bccd4129f3650
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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