Sodium hydride → 3-(2,2-Dimethoxy-ethoxy)-4'-methoxy-4-methyl-biphenyl

HRID 1372157Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([OH:18])[CH:12]=2)=[CH:7][CH:6]=1.Br[CH2:20][CH:21]([O:24][CH3:25])[O:22][CH3:23]>C1COCC1>[CH3:23][O:22][CH:21]([O:24][CH3:25])[CH2:20][O:18][C:13]1[CH:12]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:10][CH:9]=2)[CH:16]=[CH:15][C:14]=1[CH3:17]

Participants

Conditions

Temperature: 60 °C

Procedure

To NaH (357 mg (600 mg 60% in mineral oil, hexane washed 3×), 14.86 mmol) was added dry THF (100 ml), 4′-methoxy-4-methyl-biphenyl-3-ol (1.59 g, 7.43 mmol), and 2-bromo-1,1-dimethoxy ethane (1.76 g, 10.40 mmol). The reaction was stirred at 60° C. overnight, cooled, passed through a silica plug and concentrated to 1.66 g (74%) of product as a white solid: mp 3940° C.; 1H NMR (300 MHz, DMSO-d6): δ 2.17 (3H, s), 3.38 (6H, s), 3.79 (3H, s), 4.09 (2H, d, J=5.2 Hz), 4.73 (1H, t, J=5.2 Hz), 7.00 (2H, d, J=8.8 Hz), 7.09 (1H, dd, J=7.7 Hz, 1.5 Hz), 7.15 (1H, d, J=1.2 Hz), 7.18 (1H, d, J=7.8 Hz), 7.62 (2H, d, J=8.8 Hz); MS (ESI) m/z 303 ([M+H]+).

Workup

temperaturecooled
concentrationconcentrated to 1.66 g (74%) of product as a white solid

Sources & evidence

ORD record: ord-2cb2e3809d1848228c9b3416dd013201
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157491B2

Reaction notes

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