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

HRID 1248600Notes

Reaction equation

[OH:1][CH:2]([C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[C:12]([CH3:18])[C:11]=1[OH:19])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].O.[O]N(S(=O)([O-])=O)S(=O)([O-])=[O:24].[K+].[K+].Cl>[OH-].[Na+]>[CH3:18][C:12]1[C:11](=[O:19])[C:10]([CH:2]([OH:1])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[C:15]([CH3:16])[C:14](=[O:24])[C:13]=1[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-hydroxy-6-(2'-hydroxy-3',4',6'-trimethylphenyl)hexanoic acid (formula II-3 wherein R=H3C, X=H, Y=OH, n=4, in the free form) (0.158 part) in 5% sodium hydroxide solution (2 volume parts) and water (7 volume parts) was added Fremy's salt (1 part) at room temperature with stirring. After being stirred for 1 hour, the mixture was cooled to 0° C., acidified with cold dilute hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residue was subjected to column chromatography on silica gel and eluted with chloroform-methanol (20:1). The product was recrystallized from ethylacetate-hexane (1:2) to give 2,3,5-trimethyl-6-(5'-carboxy-1'-hydroxypentyl)-1,4-benzoquinone (formula I-3 wherein R=H3C, n=4, in the free form) (0.128 part) as brown needles melting at 130°-131.5° C.

Workup

stirringAfter being stirred for 1 hour
extractionextracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
washeluted with chloroform-methanol (20:1)
customThe product was recrystallized from ethylacetate-hexane (1:2)

Sources & evidence

ORD record: ord-82fccca7ea084665945b41cea0759b85
Source dataset: uspto-grants-1985_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04525361

Reaction notes

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