Hydrochloric Acid → 5-(3-Methoxyphenyl)-4-nitrovaleric acid

HRID 274071Notes

Reaction equation

HRID 274071 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([N+:20]([O-:22])=[O:21])[CH2:11][CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[CH:6]=[CH:7][CH:8]=1.Cl.[Cl-].[Na+].C(=O)([O-])O.[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([N+:20]([O-:22])=[O:21])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 20094814Tert-butyl 5-(3-methoxyphenyl)-4-nitrovalerate

Product 1

HCID 200948615-(3-Methoxyphenyl)-4-nitrovaleric acidYield 97.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 5-(3-methoxyphenyl)-4-nitrovalerate (10.00 g) in 1,4-dioxane (10 ml) was added 4N hydrogen chloride in 1,4-dioxane (17.8 ml) in an ice bath. After stirring for 3 days at ambient temperature, ice water (60 ml) and sodium chloride (6 g) was added to the solution. The pH of the solution was adjusted to 9.5 with an aqueous saturated sodium hydrogencarbonate solution and the solution was washed with ethyl acetate. After the pH of the solution was adjusted to 1 with 6N hydrochloric acid, the solution was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, treated with silica gel (20 g), and evaporated in vacuo to give 5-(3-methoxyphenyl)-4-nitrovaleric acid (8.00 g).

Workup

  1. washthe solution was washed with ethyl acetate
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. additiontreated with silica gel (20 g)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8d8aa8ff40364c3790df6f32bd84df76
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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