Hydrochloric Acid → 4-(3,4-Dimethoxyphenyl)-4-oxobutanoic acid

HRID 483362Notes

Reaction equation

HRID 483362 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[C:8]1([O:16][CH3:17])[C:9](=[CH:12][CH:13]=[CH:14][CH:15]=1)[O:10][CH3:11].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[CH3:11][O:10][C:9]1[CH:12]=[C:13]([CH:14]=[CH:15][C:8]=1[O:16][CH3:17])[C:4]([CH2:3][CH2:2][C:1]([OH:6])=[O:7])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7043VeratroleHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2193904-(3,4-Dimethoxyphenyl)-4-oxobutanoic acidYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

70 g (0.7 mol) of succinic anhydride and 96.6 g (0.7 mol) of veratrole were dissolved in 2,000 ml of methylene chloride, and 237 g (1.75 mol) of anhydrous aluminum chloride was added thereto at room temperature. The mixture was stirred at the same temperature for 6 hours. The reaction solution was left to stand for 15 hours. Then, 1,600 ml of 6N hydrochloric acid was dropwise added to the reaction solution under stirring and the mixture was further stirred for one hour. The organic layer was separated, and 300 ml of water was added thereto. The mixture was adjusted to pH7.5 with a saturated sodium bicarbonate aqueous solution. The aqueous layer was separated and adjusted to pH2.5 with 6N hydrochloric acid. The aqueous layer was left to stand in a refrigerator for two days. Then, the precipitated crystals were collected by filtration, washed with water and dried to obtain 106.8 g (yield: 64%) of 3-(3,4-dimethoxybenzoyl)propionic acid.

Workup

  1. customat room temperature
  2. waitThe reaction solution was left
  3. waitto stand for 15 hours
  4. stirringunder stirring
  5. stirringthe mixture was further stirred for one hour
  6. customThe organic layer was separated
  7. addition300 ml of water was added
  8. customThe aqueous layer was separated
  9. waitThe aqueous layer was left
  10. waitto stand in a refrigerator for two days
  11. filtrationThen, the precipitated crystals were collected by filtration
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-5619027fccc4408db0f94449c88d4fe4
Source dataset
uspto-grants-1993_07
Patent number
US05225406

Reaction notes

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