Hydrochloric Acid → 2-(3-biphenylyl)ethanol

HRID 1377036Notes

Reaction equation

HRID 1377036 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([Li])(C)(C)C.CCCCC.[CH2:24]1[O:26][CH2:25]1.Cl>C(OCC)C.O>[C:4]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=[C:2]([CH2:24][CH2:25][OH:26])[CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6354Ethylene Oxide2×HCID 8003PentaneHCID 164493-BromobiphenylHCID 178418306HCID 178418306, compound

Product 1

HCID 107031172-(3-biphenylyl)ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-bromobiphenyl (18 g, 77 mmol) in diethyl ether (150 ml) under N2 cooled to -78° C. was added 1.6M t-butyl lithium in pentane (100 ml, 0.16 mole) via cannula over a 15 minute period. The solution was stirred 30 minutes at -78° C., ethylene oxide (9 g, 0.2 mole added and the reaction mixture allowed to warm to room temperature over a 1 hour period. The solution was boiled briefly to drive off excess ethylene oxide, transferred to a separatory funnel, a small volume of water added, and neutralized with concentrated HCl. The organic solution was dried (MgSO4), concentrated in vacuo and the residue purified by chromatography on silica gel eluting with ethyl acetate:hexane (1:4) to give 2-(3-biphenylyl)ethanol (10.5 g). 1H NMR (CDCl3, 60 MHz) δ: 2.81 (t, J=7 Hz, 2H, CH2), 3.76 (t, J=7 Hz, 2H, CH2), 6.95-7.70 (m, 9H, Ar).

Workup

  1. temperatureto warm to room temperature over a 1 hour period
  2. customtransferred to a separatory funnel
  3. dry with materialThe organic solution was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by chromatography on silica gel eluting with ethyl acetate:hexane (1:4)

Sources & evidence

ORD record
ord-8568d9f7d7d54b7a83ed429d1c443986
Source dataset
uspto-grants-1997_09
Patent number
US05663337

Reaction notes

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