Hydrochloric Acid → 4-(4-Bromophenoxy)cyclohexanone

HRID 84225Notes

Reaction equation

HRID 84225 reaction equation
Cl.[Br:2][C:3]1[CH:19]=[CH:18][C:6]([O:7][CH:8]2[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH:8]2[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 672488938-(4-Bromophenoxy)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 672488834-(4-Bromophenoxy)cyclohexanoneYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1 N HCl(aq) (45 mL) was added to a solution of 8-(4-bromophenoxy)-1,4-dioxaspiro[4.5]decane (2.8 g, 8.94 mmol) in THF (100 mL). The reaction was heated to 50° C. After 1 hour the reaction was cooled to room temperature and neutralized by addition of solid sodium bicarbonate. The reaction was extracted with ether (1×), the resulting organic layer was washed with water, dried (Na2SO4), filtered and concentrated. Purification on a Biotage SNAP cartridge KP Sil 100g (hexanes/ethyl acetate=9:1) afforded the title compound as a white solid (2.09 g, 87%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.02-2.13 (m, 2 H) 2.21-2.41 (m, 4 H) 2.61-2.74 (m, 2 H) 4.62-4.71 (m, 1 H) 6.81-6.89 (m, 2 H) 7.37-7.44 (m, 2 H)

Workup

  1. temperatureAfter 1 hour the reaction was cooled to room temperature
  2. extractionThe reaction was extracted with ether (1×)
  3. washthe resulting organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification on a Biotage SNAP cartridge KP Sil 100g (hexanes/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-dd0de2fdf1a24f5695db0a170b25d76c
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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