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

HRID 1716950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1716950
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]

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 590134702-Bromo-4-(4-ethoxybenzyl)benzyl acetate

Produkt 1

HCID 59013454(2-Bromo-4-(4-ethoxybenzyl)phenyl)methanolAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. customthe volatiles were removed
  2. customa rotary evaporator
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed once with brine
  5. dry with materialdried over Na2SO4
  6. customThe volatiles were removed
  7. customa rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-664dcd452c2b4359b0481638621156dc
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803778B2

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