N,N-Dimethylglycine → 3,5-Dimethoxy-2-(5-methyl-3-methoxy-phenoxy)-4-methyl-benzoic acid methyl ester

HRID 1692617Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[C:6]([O:13][CH3:14])[C:5]=1Br.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([OH:26])[CH:22]=[C:23]([CH3:25])[CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C)CC(O)=O>[Cu]I.O.O1CCOCC1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[C:6]([O:13][CH3:14])[C:5]=1[O:26][C:21]1[CH:22]=[C:23]([CH3:25])[CH:24]=[C:19]([O:18][CH3:17])[CH:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1 mmol of 2-Bromo-3,5-dimethoxy-4-methyl-benzoic acid methyl ester, 1.5 mmol of 3-methoxy-5-methylphenol, 2 mmol of Cs2CO3, 1 mmol of CuI, and 1 mmol of N,N-dimethylglycine was added to 4 mL of dioxane under nitrogen atmosphere, and then the mixture was heated to 90° C. and monitored by TLC. Upon completion, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over Na2SO4, and evaporated by a rotary evaporator. The residue was purified by column chromatography to afford 3,5-Dimethoxy-2-(5-methyl-3-methoxy-phenoxy)-4-methyl-benzoic acid methyl ester (50%): 1H NMR (DMSO-d6) δ 7.18 (s, 1H), 6.35 (s, 1H), 6.22 (t, 1H, J=2 Hz), 6.18 (bs, 1H), 3.88 (s, 3H), 3.75 (s, 6H), 3.73 (s, 3H), 2.24 (s, 3H), 2.18 (s, 3H).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over Na2SO4
customevaporated by a rotary evaporator
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-8b132c5fba56456d85a9fb9e338f6e71
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158623B2

Reaction notes

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