Hydrochloric Acid → 4-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanone

HRID 585635Notes

Reaction equation

HRID 585635 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:24][CH2:23][C:18]2(OCC[O:19]2)[CH2:17][CH2:16]1.Cl.C(=O)(O)[O-].[Na+]>CO>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:24][CH2:23][C:18](=[O:19])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 121351698-[2,4-Bis(methoxymethoxy)phenyl]-1,4-dioxaspiro[4.5]decane

Product 1

HCID 121351704-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanoneYield 78.9%

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]decane (3.20 g 9.47 mmol) and methanol (50 ml). Over a 20 min period, aqueous hydrochloric acid (50 ml, 1.00M) was added to the stirred solution, at room temperature and the reaction mixture stirred for 1.5 hr. Solid sodium bicarbonate was added until the reaction mixture was neutralised and the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (30 ml) and water (10 ml), and the aqueous layer was extracted with ethyl acetate (3×20 ml). The combined organic layers were washed with brine (10 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:4, v/v), affording the title compound (2.20 g, 60%) as a white powder. δH(CDCl3) 1.85-1.96 (2H, m), 2.14-2.22 (2H, m), 2.46-2.59 (4H, m), 3.39 (1H, tt), 3.49 (3H, s), 3.52 (3H, s), 5.16 (2H, s), 5.23 (2H, s), 6.67-6.71 (1H, m), 6.85 (1H, m), 7.08 (1H, d).

Workup

  1. customA round bottomed flask equipped with magnetic stirrer
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (30 ml) and water (10 ml)
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×20 ml)
  5. washThe combined organic layers were washed with brine (10 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:4, v/v)

Sources & evidence

ORD record
ord-86af29fac38a4fa6b1933bd93f9ba294
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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