Hydrochloric Acid → HCID 22227323, compound

HRID 1745896Notes

Reaction equation

HRID 1745896 reaction equation
C([O:3][C:4]([C:6]([OH:15])([CH3:14])[CH2:7][CH2:8][CH2:9][O:10][CH2:11][O:12][CH3:13])=[CH2:5])C.Cl.C([O-])(O)=O.[Na+]>CO>[CH3:14][C:6]([OH:15])([CH2:7][CH2:8][CH2:9][O:10][CH2:11][O:12][CH3:13])[C:4](=[O:3])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22227318HCID 22227318, compound

Product 1

HCID 22227323HCID 22227323, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-ethoxy-3-hydroxy-6-methoxymethoxy-3-methyl-1-hexene (8.99 g. 41.2 mmol) in 50 mL of methanol was added dropwise 1 M HCl (100 mL, 100 mmol) at room temperature. The exothermic reaction was cooled by water bath and monitored by TLC. After being stirred for two hours, the resulting mixture was neutralized with NaHCO3, concentrated via rotary evaporation and extracted with 3×120 mL of dichloromethane. The combined organic layer was dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography using hexanes/ethyl acetate (2/1-1/1) as eluent to afford 4.6 g of 3-methyl-3-hydroxy-6-methoxymethoxy-2-hexanone (yield 59).

Workup

  1. customThe exothermic reaction
  2. temperaturewas cooled by water bath
  3. concentrationconcentrated via rotary evaporation
  4. extractionextracted with 3×120 mL of dichloromethane
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-bc75b3776a284520871d895a2ff39932
Source dataset
uspto-grants-2006_03
Patent number
US07019453B2

Reaction notes

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