Allyl bromide → HCID 67405223, compound

HRID 906087Notes

Reaction equation

[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O-:7])=[O:6].[CH2:12](Br)[CH:13]=[CH2:14].[C:16](=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:11][C:3]1[C:2]([O:1][CH2:12][CH:13]=[CH2:14])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH3:16])=[O:6]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-hydroxy-2-methylbenzoate (5.46 g, 33 mmol), allyl bromide (4.33 mL, 50 mmol) and cesium carbonate (21.5 g, 66 mmol) in dimethylformamide (60 mL) was stirred at 60° C. for 2.5 hours. The reaction mixture was allowed to cool to room temperature and was then partitioned between water and ethyl acetate. The aqueous portion was extracted twice using ethyl acetate, and the combined organic portion was washed with 5% aqueous lithium chloride, 1N aqueous sodium hydroxide, brine, and then was dried over sodium sulfate, filtered and concentrated in vacuo to afford (6.85 g, 100%) of methyl 2-methyl-3-(prop-2-en-1-yloxy)benzoate as a colorless oil. 1H NMR (400 MHz, DMSO-d6): 7.33-7.30 (m, 1H), 7.27-7.23 (m, 1H), 7.18-7.15 (m, 1H), 6.13-6.02 (m, 1H), 5.35 (dd, 2H), 4.61 (d, 2H), 3.82 (s, 3H), 2.35 (s, 3H). MS (EI) for C12H14O3: 207 (MH+).

Workup

temperatureto cool to room temperature
customwas then partitioned between water and ethyl acetate
extractionThe aqueous portion was extracted twice using ethyl acetate
washthe combined organic portion was washed with 5% aqueous lithium chloride, 1N aqueous sodium hydroxide, brine
dry with materialwas dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-61b1a8e192c84f0aaef2ae3dfaae1dad
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012956B2

Reaction notes

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