Water → HCID 58575472, compound

HRID 1677990Notes

Reaction equation

HRID 1677990 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-7730945d827f453b9bd3dc9fd27f3900
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

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