Hydrochloric Acid → 5-(3,4-Dimethoxyphenyl)-5-oxovaleric acid

HRID 1195956Notes

Reaction equation

HRID 1195956 reaction equation
[C:1]1([O:9][CH3:10])[C:2](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O:3][CH3:4].[C:11]1(=[O:18])[O:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12]1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](C1C=CC=CC=1)([O-])=O>[CH3:4][O:3][C:2]1[CH:5]=[C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:7]=[CH:8][C:1]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7043VeratroleHCID 7940Glutaric anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27584705-(3,4-Dimethoxyphenyl)-5-oxovaleric acid

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Procedure

A solution containing 36 g of veratrole and 30 g glutaric anhydride in 120 ml of nitrobenzene was gradually added while stirring and cooling at 0° C. to a mixture of 72 g of anhydrous aluminum chloride and 240 ml of nitrobenzene. The mixture was stirred for 1 h at 0° C. and then for 18 h at 20° C. Ice and hydrochloric acid were added to the reaction mixture. Nitrobenzene layer was separated and to this ethyl acetate was added whereupon the product crystallized. After filtering the crystals were washed with ethyl acetate. Yield 42.3 g (64%).

Workup

  1. additionwas gradually added
  2. stirringThe mixture was stirred for 1 h at 0° C.
  3. customNitrobenzene layer was separated and to this ethyl acetate
  4. additionwas added whereupon the product
  5. customcrystallized
  6. filtrationAfter filtering the crystals
  7. washwere washed with ethyl acetate

Sources & evidence

ORD record
ord-117eeba72cc54d508e68089d5d6f656e
Source dataset
uspto-grants-1992_05
Patent number
US05112861

Reaction notes

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