Potassium Hydroxide → 6-[2-(2,6,6-Trimethylcyclohex-1-enyl)ethynyl]-2-naphthoic acid

HRID 2399769Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16]#[C:17][C:18]3[C:23]([CH3:25])([CH3:24])[CH2:22][CH2:21][CH2:20][C:19]=3[CH3:26])[CH:12]=2)[CH:7]=1)=[O:5])C.[OH-].[K+]>C(O)C.O>[CH3:26][C:19]1[CH2:20][CH2:21][CH2:22][C:23]([CH3:24])([CH3:25])[C:18]=1[C:17]#[C:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:15]=[CH:14]2

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 0.130 g (0.38 mmol) of ethyl-6-[2-(2,6,6-trimethylcyclohex-1-enyl)ethynyl]-2-naphthoate (Compound 3) in 0.7 ml of ethanol was added dropwise under nitrogen 0.9 ml of a 1.86M solution of KOH in ethanol and water. After being stirred at 50 degrees C. for 18 hours, solvent was removed in-vacuo and the residue treated with 1 ml of water and extracted with 1×3 ml portions of ether. The aqueous layer was then acidified with dilute HCl and extracted with 3×3 ml portions of ether. Combined ether extracts were dried (MgSO4), filtered, and concentrated in-vacuo to give the title product.

Workup

customsolvent was removed in-vacuo
additionthe residue treated with 1 ml of water
extractionextracted with 1×3 ml portions of ether
extractionextracted with 3×3 ml portions of ether
dry with materialCombined ether extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in-vacuo

Sources & evidence

ORD record: ord-8c5c4cfced76485f968a2f607e43f7a1
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05451605

Reaction notes

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