Lithium hydroxide, monohydrate → (2-Bromo-4-(4-ethoxybenzyl)phenyl)methanol

HRID 1716950Notes

Reaction equation

C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:8][C:7]=1[Br:22])(=O)C.O[Li].O>C1COCC1.CO.O>[Br:22][C:7]1[CH:8]=[C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)[CH:10]=[CH:11][C:6]=1[CH2:5][OH:4]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-bromo-4-(4-ethoxybenzyl)benzyl acetate (0.215 g, 0.59 mmol) in 10 mL of THF/MeOH/H2O (2:3:1) was added LiOH.H2O (0.051 g, 1.21 mmol). After the reaction mixture was stirred at 25° C. for 3 hours, the volatiles were removed using a rotary evaporator. The residue was dissolved in EtOAc, washed once with brine and dried over Na2SO4. The volatiles were removed using a rotary evaporator to yield 0.175 g of the title compound, which was used in the next step without further purification. 1H NMR (CDCl3, 300 MHz): δ 7.38-7.36 (m, 2H), 7.13 (d, J=7.6 Hz, 1H), 7.07 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.4 Hz, 2H), 4.71 (s, 2H), 4.01 (q, J=7.2 Hz, 2H), 3.88 (s, 2H), 1.92 (bs, 1H), 1.40 (t, J=7.2 Hz, 3H); MS ESI (m/z) 320 [M+], calc. 320.

Workup

customthe volatiles were removed
customa rotary evaporator
dissolutionThe residue was dissolved in EtOAc
washwashed once with brine
dry with materialdried over Na2SO4
customThe volatiles were removed
customa rotary evaporator

Sources & evidence

ORD record: ord-664dcd452c2b4359b0481638621156dc
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803778B2

Reaction notes

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