Water → 4-(2,4-Dihydroxyphenyl)cyclohexanone

HRID 585686

Reaction equation

HRID 585686 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=3[OH:18])[CH2:7][CH2:6]2)[O:4]CC1.O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O>[OH:18][C:12]1[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=1[CH:8]1[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 99212574-(1,4-Dioxaspiro[4.5]dec-8-yl)-1,3-benzenediol

Product 1

HCID 99424894-(2,4-Dihydroxyphenyl)cyclohexanoneYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A round bottomed flask equipped with magnetic stirrer was charged with 4-(1,4-dioxaspiro[4.5]dec-8-yl)-1,3-benzenediol (11.3 g, 45.2 mmol), acetone (250 ml) and water (50 ml). To the stirred solution was added pyridinium p-toluenesulfonate (1.14 g, 4.52 mmol) in one portion and the reaction mixture was then heated to reflux temperature for 8 hr. After allowing the reaction mixture to cool to room temperature, most of the acetone was removed in vacuo and the remaining mixture was partitioned between ethyl acetate (200 ml) and water (50 ml). The aqueous layer was extracted with ethyl acetate (3×50 ml) and the combined organic layers were washed with brine (30 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford an off white powder. After washing the powder with dichloromethane (100 ml) and removal of excess solvent under reduced pressure, the desired product (9.30 g, 100%) was obtained as an off-white white powder. m/z (ES+) 207 (M+H+); δH(CD3OD) 1.84-1.97 (2H, m), 2.15-2.23 (2H, m), 2.36-2.45 (2H, m), 2.58-2.68 (2H, m), 3.39 (1H, tt), 6.26 (1H, dd), 6.34 (1H, d), 6.96 (1H, d).

Workup

  1. customA round bottomed flask equipped with magnetic stirrer
  2. temperaturethe reaction mixture was then heated
  3. temperatureto reflux temperature for 8 hr
  4. customwas removed in vacuo
  5. customthe remaining mixture was partitioned between ethyl acetate (200 ml) and water (50 ml)
  6. extractionThe aqueous layer was extracted with ethyl acetate (3×50 ml)
  7. washthe combined organic layers were washed with brine (30 ml)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto afford an off white powder
  12. washAfter washing the powder
  13. customwith dichloromethane (100 ml) and removal of excess solvent under reduced pressure

Sources & evidence

ORD record
ord-8f4b9153cc9a412eb41a59f49848f925
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Linked notes

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