Sulfuric Acid → HCID 67057766, compound

HRID 604671Notes

Reaction equation

HRID 604671 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:18][CH2:17][C:12]3(OCC[O:13]3)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].S(=O)(=O)(O)O>CC(C)=O.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:10][CH2:11][C:12](=[O:13])[CH2:17][CH2:18]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 67057702HCID 67057702, compound

Product 1

HCID 67057766HCID 67057766, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-(3-chloro-4-fluorophenyl)-1,4-dioxaspiro[4.5]decane (401.7 mg, 1.484 mmol) in acetone (6 ml) was added 1M sulfuric acid (24 ml, 24 mmol). The reaction was stirred vigorously at room temperature for 18 hours, and then diluted with EtOAc (100 mL) and washed with water (3×50 mL), saturated NaHCO3 (2×50 mL), and brine (2×50 mL). The organic layer was dried (Na2SO4), filtered, and concentrated to afford 4-(3-chloro-4-fluorophenyl)cyclohexanone. 1H NMR (500 MHz, CDCl3): δ 7.06-7.28 (m, 3H), 3.00 (m, 1H), 2.49-2.52 (m, 4H), 2.19-2.23 (m, 2H), 1.85-1.93 (m, 2H).

Workup

  1. washwashed with water (3×50 mL), saturated NaHCO3 (2×50 mL), and brine (2×50 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-07e83e77cb5245bb936a4178f93eba05
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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