Hydrochloric Acid → 4-(2-Methoxyethoxy)cyclohexanone

HRID 2070090Notes

Reaction equation

HRID 2070090 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH2:5][O:6][CH:7]1[CH2:16][CH2:15][C:10]2(OCC[O:11]2)[CH2:9][CH2:8]1>O1CCCC1>[CH3:2][O:3][CH2:4][CH2:5][O:6][CH:7]1[CH2:16][CH2:15][C:10](=[O:11])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 594440998-(2-Methoxyethoxy)-1,4-dioxa-spiro[4.5]decane

Product 1

HCID 138222284-(2-Methoxyethoxy)cyclohexanoneYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 10 L round-bottomed flask 8-{[2-(methyloxy)ethyl]oxy}-1,4-dioxaspiro[4.5]decane D20 (151 g, 700 mmol) was dissolved in tetrahydrofuran (THF) (3000 mL) to give a colourless solution. 3M hydrochloric acid (2333 mL, 7000 mmol) was added. Reaction was allowed to stir at room temperature overnight. The organic solvent was partially evaporated under vacuum and then the aqueous layer was back extracted with DCM (3×500 mL). The organic phase was dried over Na2SO4, filtered and concentrated to obtain 121 g of crude material as yellow oil. The crude product was purified by Biotage® 75 L SiO2 column eluting with c-hex/EtOAc 8/2 to get title material (76 g; 63%).

Workup

  1. customto give a colourless solution
  2. customReaction
  3. customThe organic solvent was partially evaporated under vacuum
  4. extractionthe aqueous layer was back extracted with DCM (3×500 mL)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto obtain 121 g of crude material as yellow oil
  9. customThe crude product was purified by Biotage® 75 L SiO2 column
  10. washeluting with c-hex/EtOAc 8/2

Sources & evidence

ORD record
ord-079641760ed34c81a1f515ec60fd22e7
Source dataset
uspto-grants-2012_10
Patent number
US08299257B2

Reaction notes

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