Hydrochloric Acid → HCID 12906150, compound

HRID 1390566Notes

Reaction equation

N(S([O-])(=O)=O)(S([O-])(=O)=O)[O].[K+].[K+].[OH:13][C:14]1[C:19]([CH3:20])=[C:18]([CH3:21])[CH:17]=[C:16]([CH3:22])[C:15]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29].[OH2:31].Cl>[OH-].[Na+]>[CH3:20][C:19]1[C:14](=[O:13])[C:15]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[C:16]([CH3:22])[C:17](=[O:31])[C:18]=1[CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

Potassium nitrosodisulfonate (0.9 part) was added to a solution of 6-(2'-hydroxy-3',4',6'-trimethylphenyl)hexanoic acid (formula II-2 wherein R=H3C, X=H, Y=OH, n=4, in the free form) (0.111 part) in 1% sodium hydroxide (5 volume parts) and water (3 volume parts) and the mixture was stirred at room temperature for 30 minutes. Then, the reaction mixture was cooled to 0° C. and, following the addition of cold water (50 volume parts), it was rendered acidic with dilute hydrochloric acid, whereupon a yellow precipitate was obtained. Recrystallization of this precipitate from hexane-ethyl acetate (10:1) provided 2,3,5-trimethyl-6-(5'-carboxypentyl)-1,4-benzoquinone (formula I-2 wherein R=H3C, n=4, in the free form) (0.11 part) as yellow needles melting at 81°-82° C.

Workup

customwas obtained
customRecrystallization of this precipitate from hexane-ethyl acetate (10:1)

Sources & evidence

ORD record: ord-3143e5d8e60d4a4ba543ce9aacc299fe
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04139545

Reaction notes

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