Sodium Hydroxide → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

HRID 1614889Notes

Reaction equation

[O-:1][Mn](=O)(=O)=O.[K+].[CH3:7][C:8]1([CH3:21])[CH2:17][CH2:16][C:15]([CH3:19])([CH3:18])[C:14]2[CH:13]=[C:12]([CH3:20])[CH:11]=[CH:10][C:9]1=2.[OH-:22].[Na+]>N1C=CC=CC=1>[CH3:7][C:8]1([CH3:21])[CH2:17][CH2:16][C:15]([CH3:19])([CH3:18])[C:14]2[CH:13]=[C:12]([C:20]([OH:1])=[O:22])[CH:11]=[CH:10][C:9]1=2

Participants

Conditions

Temperature: 95 °C

Procedure

The synthesis process is as set forth in the chemical reaction formula below. The KMnO4 in the reaction path stands for potassium permanganate. To 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-methylnaphthalene (3.52 g, 17.4 mmol) were added pyridine (12 mL), potassium permanganate (6.70 g, 42.4 mmol), and sodium hydroxide (1.00 g, 25.0 mmol) followed by stirring at 95° C. for 5 hours. The reaction solution was filtrated by celite and the filtrate was made acidic by adding hydrochloric acid. After extraction by ethyl acetate, the liquid was dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography using hexane/ethyl acetate (4/1) as an elution solvent. The yield was 141.6 mg (3%).

Workup

filtrationThe reaction solution was filtrated by celite
additionby adding hydrochloric acid
extractionAfter extraction by ethyl acetate
dry with materialthe liquid was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-a8ca9bdf5ab14709826d641b7c67819d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765719B2

Reaction notes

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