Ethanol → HCID 18624146, compound

HRID 1860688Notes

Reaction equation

HRID 1860688 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([CH3:16])([CH3:15])[CH2:12][CH:13]=[O:14].[OH-].[Na+].[CH2:19]([OH:21])[CH3:20]>O.Cl.O1CCOCC1.[N+]([O-])([O-])=O.[Ag+]>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([CH3:16])([CH3:15])[CH2:12][C:13]([O:21][CH2:19][CH3:20])=[O:14]

Participants

8

Reactant 3

HCID 702Ethanol2×HCID 14798Sodium HydroxideHCID 18624203HCID 18624203, compound

Product 1

HCID 18624146HCID 18624146, compoundYield 71%

Reagents, catalysts & solvents 4

HCID 24470Silver NitrateCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Silver nitrate (21 g, 124 mmoles) was dissolved in 35 mL H2O and added to a solution of 4-(2-bromo-4-methoxyphenyl)-3,3-dimethylbutanal (11 g, 38.6 mmoles) in 250 mL ethanol. A solution of NaOH (10 g, 250 mmoles) in 35 mL of H2O was added dropwise, then the reaction was stirred at room temperature for 2 hours. The reaction was passed through a short pad of Celite. Then, the ethanol was evaporated and the residue was partioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate (2×200 mL). The organic layers were discarded. The water layer was acidified with 2 N HCl solution to pH=2, and extracted with ethyl acetate (3×200 mL). The organic extracts were washed with brine, dried (Na2SO4), and concentrated to afford an oil. The oil was dissolved in 60 mL of 4N HCl in dioxane and 120 mL of absolute ethanol overnight at 25° C. The reaction was evaporated to dryness then taken up in ethyl acetate and extracted with a saturated solution of aqueous sodium bicarbonate, brine, dried (Na2SO4), and evaporated to give 9.1 g (71%) of the desired compound. NMR spectrum of the product was consistent for the proposed structure.

Workup

  1. customThen, the ethanol was evaporated
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×200 mL)
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. washThe organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto afford an oil
  8. customat 25° C
  9. customThe reaction was evaporated to dryness
  10. extractionextracted with a saturated solution of aqueous sodium bicarbonate, brine
  11. dry with materialdried (Na2SO4)
  12. customevaporated

Sources & evidence

ORD record
ord-3d83a8c4497e4247ae359aee2607c6a1
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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