Hydrochloric Acid → 2-(3-biphenylyl)ethanol

HRID 2289228Notes

Reaction equation

HRID 2289228 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 1.6 M t-butyl lithium in pentane (100 ml, 0.16 mole) vi a 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 a nd 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 a nd the residue
  5. custompurified by chromatography on silica gel eluting with ethyl acetate:hexane (1:4)

Sources & evidence

ORD record
ord-69d54080ea9a4b78a51e255c0aaeed0d
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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