Hydrochloric Acid → 2,3,5-Trimethyl-6-(5'-carboxy-1'-oxopentyl)-1,4-benzoquinone

HRID 1248591Notes

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

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

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

Sources & evidence

ORD record: ord-9ba1392482e2429db9579a99c1a24482
Source dataset: uspto-grants-1985_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04525361

Reaction notes

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