Diisobutylaluminum hydride → 2-(4-Phenylphenoxy)ethanol

HRID 459139Notes

Reaction equation

HRID 459139 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)C.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:10]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][OH:3])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 765876Ethyl (biphenyl-4-yloxy)acetate

Product 1

HCID 3029632-(4-Phenylphenoxy)ethanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of (Biphenyl-4-yloxy)-acetic acid ethyl ester (0.63 g, 2.46 mmol) in dry toluene (15 mL) at −78° C. was added DIBAL-H 1M in toluene (4.92 mL, 4.92 mmol). The solution was stirred at −78° C. for 1 hour, warmed to room temperature and quenched with mixture of a solution of sodium tartrate in water and ethyl acetate for 1 hour. The layers were separated and the aqueous phase further extracted with ethyl acetate. The combined organic layers were dried (MgSO4), concentrated under vacuum and the residue purified bu column chromatography (silica gel, hexanes/Ethyl acetate 4:1, Rf0.1), 48%. 1H-NMR (CDCl3, 200.15 MHz): 7.58–7.26 (m, 8H); 7.00 (d, 2H, J=8.6), 4.14 (t, 2H, J=4.6), 4.02–3.98 (m, 2H); 2.04 (t, 1H, J=5.4).

Workup

  1. temperaturewarmed to room temperature
  2. customquenched with mixture of a solution of sodium tartrate in water and ethyl acetate for 1 hour
  3. customThe layers were separated
  4. extractionthe aqueous phase further extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. customthe residue purified bu column chromatography (silica gel, hexanes/Ethyl acetate 4:1, Rf0.1), 48%

Sources & evidence

ORD record
ord-2484a88e82574949af538a0e1631053c
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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