Hydrochloric Acid → 4-(2,4-Dihydroxyphenyl)-3-cyclohexen-1-one

HRID 585684Notes

Reaction equation

HRID 585684 reaction equation
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[C:15]1[CH2:24][CH2:23][C:18]2(OCC[O:19]2)[CH2:17][CH:16]=1.Cl.C(=O)(O)[O-].[Na+]>CO>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[C:15]1[CH2:24][CH2:23][C:18](=[O:19])[CH2:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 121351688-[2,4-Bis(methoxymethoxy)phenyl]-1,4-dioxaspiro[4.5]dec-7-ene

Product 1

HCID 223378184-(2,4-Dihydroxyphenyl)-3-cyclohexen-1-oneYield 37.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A round bottomed flask equipped with magnetic stirrer was charged with 8-[2,4-bis(methoxymethoxy)phenyl]-1,4-dioxaspiro[4.5]dec-7-ene (1.50 g, 4.24 mmol) and methanol (30 ml). To the stirred solution was added aqueous hydrochloric acid (30 ml, 1.0M) and the solution was heated to reflux temperature for 1.5 hr. After cooling to room temperature, saturated aqueous sodium bicarbonate (20 ml) was added and the layers separated. The aqueous layer was extracted with ethyl acetate (4×20 ml) and the combined organic layers washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting oil was purified via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:3, v/v) to afford the title compound as a yellow solid (323 mg, 37%). m/z (ES−) 203 (M−H+); δH(CD3OD) 2.62 (2H, t), 2.86 (2H, t), 3.04 (2H, m), 5.78 (1H, m), 6.28 (1H, m), 6.32 (1H, m), 6.96 (1H, d).

Workup

  1. customA round bottomed flask equipped with magnetic stirrer
  2. temperaturethe solution was heated
  3. temperatureto reflux temperature for 1.5 hr
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted with ethyl acetate (4×20 ml)
  6. washthe combined organic layers washed with brine (20 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting oil was purified via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:3

Sources & evidence

ORD record
ord-6e80b6fe6a234458b6900d43c5833abd
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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