Sulfuric Acid → HCID 57825044, compound

HRID 1668738Notes

Reaction equation

HRID 1668738 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:8]=[C:9]([C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([CH3:25])[CH:18]=2)(O)[CH3:15])[CH:10]=[CH:11][C:12]=1[Cl:13]>CO>[Br:6][C:7]1[CH:8]=[C:9]([C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([CH3:25])[CH:18]=2)=[CH2:15])[CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 57825194HCID 57825194, compound

Product 1

HCID 57825044HCID 57825044, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated sulfuric acid (1.5 mL) was added cautiously to a stirred solution of 1-(3-bromo-4-chlorophenyl)-1-(4-methoxy-3-methylphenyl)-ethanol (6.7 g, 0.019 mol) in methanol (200 mL). The reaction mixture was stirred at reflux for 90 minutes then concentrated to remove methanol. The residue was partitioned between hexane (100 mL) and water (150 mL) and the layers separated. The aqueous fraction was extracted with hexane (2×75 mL) and the combined organic extracts were washed with brine (75 mL), dried (sodium sulfate) and concentrated to give the crude product as a yellow oil, which was purified by dry flash chromatography (0 to 1% ethyl acetate/hexane) to give the alkene as a slowly crystallising colourless oil (4.5 g, 70%), mp 79-81° C. 1H NMR (300 MHz; CDCl3) 7.61 (1H, d, J 2.1, Ar), 7.39 (1H, d J 8.3, Ar), 7.21 (1H, dd J 8.3 & 2.1, Ar), 7.09-7.06 (2H, m, Ar), 6.79 (1H, d, J 8.3, Ar), 5.41 (1H, s, olefinic), 5.33 (1H, s, olefinic), 3.85 (3H, s, OMe), 2.21 (3H, s, Me).

Workup

  1. temperatureat reflux for 90 minutes
  2. concentrationthen concentrated
  3. customto remove methanol
  4. customThe residue was partitioned between hexane (100 mL) and water (150 mL)
  5. customthe layers separated
  6. extractionThe aqueous fraction was extracted with hexane (2×75 mL)
  7. washthe combined organic extracts were washed with brine (75 mL)
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated
  10. customto give the crude product as a yellow oil, which
  11. customwas purified
  12. dry with materialby dry flash chromatography (0 to 1% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2b0a2584e94e404fafaa1c0729a4377a
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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