Hydrochloric Acid → HCID 12906149, compound

HRID 647043Notes

Reaction equation

HRID 647043 reaction equation
[OH:1][C:2]1[C:16]([CH3:17])=[C:15]([CH3:18])[CH:14]=[C:13]([CH3:19])[C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:5].N(S([O-])(=O)=O)(S([O-])(=O)=[O:23])[O].[K+].[K+].Cl>[OH-].[Na+].O>[CH3:17][C:16]1[C:2](=[O:1])[C:3]([C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[C:13]([CH3:19])[C:14](=[O:23])[C:15]=1[CH3:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3032624Potassium nitrosodisulfonateHCID 12906148HCID 12906148, compound

Product 1

HCID 12906149HCID 12906149, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

5-(2'-Hydroxy-3',4',6'-trimethylbenzoyl)pentanoic acid (formula II-1 wherein R=H3C, X=H, Y=OH, n=4, in the free form) (0.048 part) was dissolved in 0.5% NaOH (3.3 volume parts) and, while the solution was stirred at 20° C., potassium nitrosodisulfonate (0.4 part) was added. The mixture was stirred for 10 minutes. Then, under cooling with ice, the reaction mixture was diluted with water (100 volume parts) and rendered acidic with dilute hydrochloric acid. It was then extracted with diethyl ether and the extract was washed with water and dried. The solvent was distilled off under reduced pressure and the residue was then recrystallized from hexane-ethyl acetate (2:1). The procedure provided 2,3,5-trimethyl-6-(5'-carboxy-1'-oxopentyl)-1,4-benzoquinone (formula I-1 wherein R=H3C, n=4, in the free form) (0.042 part) as yellow needles melting at 96.5°-98.5° C.

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. temperatureThen, under cooling with ice
  3. extractionIt was then extracted with diethyl ether
  4. washthe extract was washed with water
  5. customdried
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was then recrystallized from hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-b848c61be6a84839927606acc4fb8798
Source dataset
uspto-grants-1983_10
Patent number
US04407757

Reaction notes

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