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

HRID 1263519Notes

Reaction equation

HRID 1263519 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 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A round bottomed flask was charged with 8-[2,4-bis(methoxymethoxy)phenyl]-1,4-dioxaspiro[4.5]decane (3.20 g) and methanol (50 ml). Over a 20 min period, aqueous hydrochloric acid (50 ml, 1M) 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. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate (30 ml) and water (10 ml)
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×20 ml)
  4. washThe combined organic layers were washed with brine (10 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:4, v/v)

Sources & evidence

ORD record
ord-5601ffba3bb44420964dffcd6251a585
Source dataset
uspto-grants-2003_04
Patent number
US06541473B2

Reaction notes

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