2,3-Dimethylphenol → HCID 86649464, compound

HRID 2190911Notes

Reaction equation

[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10]([O:12][C:13](=[O:25])[CH:14]([C:20](OCC)=[O:21])[C:15](OCC)=[O:16])[CH3:11].[Sn](Cl)(Cl)(Cl)Cl>>[CH2:10]([O:12][C:13]([C:14]1[C:15](=[O:16])[O:9][C:3]2[C:4]([C:20]=1[OH:21])=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=2[CH3:1])=[O:25])[CH3:11]

Participants

Reactant 3

HCID 106872,3-Dimethylphenol

HCID 24287Tin tetrachloride

HCID 80471Triethyl methanetricarboxylate

Product 1

HCID 86649464HCID 86649464, compoundYield 0.7%

Conditions

Temperature: 200 °C

Procedure

A mixture of 2,3-dimethyl-phenol (1.17 g, 9.57 mmol), 2-ethoxycarbonyl-malonic acid diethyl ester (4.1 mL, 19.1 mmol), and tin tetrachloride (23 μL, 0.19 mmol) was heated in a 200° C.-oil bath for 10 min; then cooled, the reaction mixture was directly purified on silica gel column chromatography (eluent: ethyl acetate in dichloromethane: 20% to 80%) to give the desired title product (18 mg). ESI (m/z): 263 (M+H)+.

Workup

temperaturethen cooled
customthe reaction mixture was directly purified on silica gel column chromatography (eluent: ethyl acetate in dichloromethane: 20% to 80%)

Sources & evidence

ORD record: ord-1a24f15f947c48a6a4ca3abca380fe37
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324405B2

Reaction notes

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