Hydrochloric Acid → 1-Methyl-2-((2-methylphenoxy)methyl)benzene

HRID 1160296Notes

Reaction equation

Br[CH2:2][C:3]1[C:4]([CH3:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C.O>[CH3:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

α-bromo-o-xylene (2.0 g, 10.81 mmol) was added to a solution of 2-methyl-phenol (1.06 g, 9.82 mmol) and cesium carbonate (7.99 g, 24.55 mmol) in DMF (20 mL). The reaction was stirred at 80° C. overnight. The reaction mixture was acidified with 25 mL 1N HCl(aq) and poured into copious water. The aqueous layer was extracted with ethyl acetate and the organic layer was dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified via radial chromatography (20% ethyl acetate in hexanes) to yield 1.82 g (88%) of 2-(2-methyl-benzyloxy)toluene (31.1). LC/MSD m/e: 213.2 (M+H).

Workup

extractionThe aqueous layer was extracted with ethyl acetate
dry with materialthe organic layer was dried (Na2SO4)
concentrationconcentrated in vacuo
customThe resulting residue was purified via radial chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-21e5f613ff49479fb08ae5941c2acc15
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816367B2

Reaction notes

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