Diethyl Ether → 2-Phenylethanol

HRID 604996Notes

Reaction equation

HRID 604996 reaction equation
[Si](OC[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.C([Mg]Cl)C1C=CC=CC=1.[CH2:27]([O:29]CC)C.[Cl-].[NH4+]>O1CCCC1.O>[C:13]1([CH2:14][CH2:27][OH:29])[CH:12]=[CH:11][CH:10]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 108687284-(((tert-Butyl(dimethyl)silyl)oxy)methyl)benzaldehydeHCID 178418336HCID 178418336, compound

Product 1

HCID 60542-Phenylethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

4-(t-Butyldimethylsilyloxymethyl)benzaldehyde (Synthesis (1995), 12, 1529-33) (6.65 gm, 26 mmol) was dissolved in dry tetrahydrofuran (50 mL) and the solution cooled to −40° C. Benzyl magnesium chloride in diethyl ether (1 M, 35 mL, 35 mmol) was added slowly. The reaction was allowed to warm to 0° C. over three hours. The reaction was then quenched by the addition of ammonium chloride (2.3 gm, 43 mmol) in water (60 mL). The product was extracted into diethyl ether, washed with NaHCO3 solution, dried (over Na2SO4), and filtered. The solution was evaporated to give 1-[4-t-butyldimethylsilyloxymethyl)-phenyl]-2-phenylethanol as an oil which was used as is. 1H-NMR (500 MHz, CDCl3): δ 7.19-7.34 (9H, m), 4.90 (1H, dd, J=4.9, 8.3 Hz), 4.75 (2H, s), 2.98-3.07 (2H, dt), 0.95 (6H, s), 0.11 (9H, s).

Workup

  1. temperatureto warm to 0° C. over three hours
  2. extractionThe product was extracted into diethyl ether
  3. washwashed with NaHCO3 solution
  4. dry with materialdried (over Na2SO4)
  5. filtrationfiltered
  6. customThe solution was evaporated

Sources & evidence

ORD record
ord-8c2f3d8158f844c48733b71d15a8af7d
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

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