Water → 4-Methoxy-gamma-oxobenzenebutanoic acid

HRID 2396567Notes

Reaction equation

HRID 2396567 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[N+]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-].[OH2:21].Cl[CH:23](Cl)C(Cl)Cl>>[O:21]([C:11]1[CH:16]=[CH:15][C:14]([C:1]([CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:7])=[CH:13][CH:12]=1)[CH3:23]

Participants

6

Reactant 5

HCID 962WaterHCID 65911,1,2,2-TetrachloroethaneHCID 7416NitrobenzeneHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 766134-Methoxy-gamma-oxobenzenebutanoic acidYield 88%

Procedure

A solution of p-anisole (4.32 g, 50 mmol) and succinic anhydride (4.14 g, 40 mmol) were combined in 1,1,2,2-tetrachloroethane (10 mL) and nitrobenzene (40 mL) at 4° C. Aluminum chloride (24.56 g, 180 mmol) was then added gradually. The temperature was kept at 0°-5° C. and stirred overnight. Water was added and neutralized to quench the reaction. The aqueous phase was separated and washed with ether then reacidified and washed with ether again. The ether fractions were combined, dried and evaporated. The remaining residue was purified by flash silica chromatography to yield a white solid (7.55 g, 88%). 1H NMR (CDCl3) δ 7.98 (d, 3H), 6.88 (d, 2H), 3.76 (s, 3H), 3.30 (t, 2H), 2.76 (t, 2H).

Workup

  1. customat 4° C
  2. customwas kept at 0°-5° C.
  3. customto quench
  4. customthe reaction
  5. customThe aqueous phase was separated
  6. washwashed with ether
  7. washwashed with ether again
  8. customdried
  9. customevaporated
  10. customThe remaining residue was purified by flash silica chromatography

Sources & evidence

ORD record
ord-64b067a1a93b491a8f74a8b0c0da041a
Source dataset
uspto-grants-1996_02
Patent number
US05493012

Reaction notes

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