Hydrochloric Acid → 3-Iodo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1075620Notes

Reaction equation

Cl([O-])(=O)(=O)=O.[Na+].[CH3:7][C:8]1([CH3:21])[CH2:17][CH2:16][C:15]([CH3:19])([CH3:18])[C:14]2[CH:13]=[C:12]([OH:20])[CH:11]=[CH:10][C:9]1=2.[OH-].[Na+].[I-:24].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>CO>[I:24][C:11]1[C:12]([OH:20])=[CH:13][C:14]2[C:15]([CH3:19])([CH3:18])[CH2:16][CH2:17][C:8]([CH3:21])([CH3:7])[C:9]=2[CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 3.6% sodium perchlorate solution was added dropwise to a mixture of 5,5,8,8-tetramethyl-5,6,7,8tetrahydronaphthalen-2-ol(6.35 g, 31.1 mmol), sodium hydroxide (1.23 g, 34.2 mmol) and sodium iodide (4.6 g, 31.1 mmol) in methanol (115 ml), at 0° C. The mixture was maintained under stirring for two hours at 0° C. 33 ml of a 10% sodium thiosulfate solution were added. After stirring, the mixture was acidified with hydrochloric acid to pH 1. It was extracted with 200 ml of ethyl ether. The organic phase was washed twice with 400 ml of water, dried over magnesium sulfate and concentrated in a rotary evaporator under vacuum at 40° C.

Workup

temperatureThe mixture was maintained
stirringAfter stirring
extractionIt was extracted with 200 ml of ethyl ether
washThe organic phase was washed twice with 400 ml of water
dry with materialdried over magnesium sulfate
concentrationconcentrated in a rotary evaporator under vacuum at 40° C.

Sources & evidence

ORD record: ord-51aa7c0bd8c94e34936dc0a39f0005f5
Source dataset: uspto-grants-1999_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05905088

Reaction notes

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