Hydrochloric Acid → Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoate

HRID 9628Notes

Reaction equation

C([O:4][C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]([CH3:20])[CH:6]=1)(=O)C.[O-]CC.[Na+].Cl>C(O)C>[OH:4][C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]([CH3:20])[CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of ethyl 2-[4-(acetyloxy)-2-methylphenoxy]-2-methylpropanoate (intermediate 9, 40.8 g) in ethanol (280 ml) was treated with sodium ethoxide (12.9 g) at room temperature under nitrogen. The resulting solution was heated to 50° C. for 1 hour. 2M hydrochloric acid (95 ml) was added to the cooled reaction and the solution concentrated. The residue was dissolved in t-butylmethyl ether and the resulting solution washed with water followed by brine and then dried over sodium sulfate, filtered and the filtrate concentrated to give a brown oil. Further purification by Biotage® chromatography eluting initially with cyclohexane and then cyclohexane:ethyl acetate (5:1) gave the title compound as an orange oil.

Workup

concentrationthe solution concentrated
dissolutionThe residue was dissolved in t-butylmethyl ether
washthe resulting solution washed with water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationthe filtrate concentrated
customto give a brown oil
customFurther purification by Biotage® chromatography
washeluting initially with cyclohexane

Sources & evidence

ORD record: ord-cde935c22f454ba4aabd0f9182db7aa1
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091237B2

Reaction notes

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