Hydrochloric Acid → Hydrochloric Acid

HRID 871058Notes

Reaction equation

HRID 871058 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:17])[O:16][C:14](=[O:15])[CH2:13][CH2:12]1.[Cl-:18].[Al+3].[Cl-].[Cl-].Cl>[N+](C1C=CC=CC=1)([O-])=O>[ClH:18].[CH3:4][O:3][C:2]1[CH:5]=[C:6]([C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:7]=[CH:8][C:1]=1[O:9][CH3:10]

Participants

7

Reactant 4

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

Product 2

HCID 313Hydrochloric AcidHCID 2193904-(3,4-Dimethoxyphenyl)-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

Veratrole (7 g, 0.05 mol) was added dropwise over 30 min to a stirred suspension of succinic anhydride (6 g, 0.6 mol) and Aluminium chloride (16 g, 0.12 mol) in 40 ml of nitrobenzene at 10° C. The temperature was then slowly raised to room temperature and was stirred at room temperature for 12 hours. The reaction mixture was then poured over ice cold water and then acidified with Con HCl. The solid product was filtered off and then redissolved in 1 N NaOH and extracted with ether. The ethereal layer was discarded and the aqueous layer was acidified with Con. HCl to obtain the required product. The pale yellow product was filtered and dried.

Workup

  1. additionThe reaction mixture was then poured over ice cold water
  2. filtrationThe solid product was filtered off
  3. dissolutionredissolved in 1 N NaOH
  4. extractionextracted with ether

Sources & evidence

ORD record
ord-a24c5ec8457f451baffcea9f13d4b016
Source dataset
uspto-grants-2015_03
Patent number
US08969573B2

Reaction notes

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