Ethylene Oxide → [1,1'-Biphenyl]-2-ethanol
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Mg].[CH2:15]1[O:17][CH2:16]1.[Cl-].[NH4+]>C1COCC1.C(OCC)C.Cl>[C:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH2:15][CH2:16][OH:17]Participants
Conditions
- Temperature
- 0 °C
Procedure
2-Bromobiphenyl (20.0 g, 86 mmol) in THF (85 ml) was dropwise added to a refluxing suspension of magnesium (2.1 g, 86 mmol) in THF (15 ml). The reaction mixture was refluxed for 18 h and an extra batch of 2-bromobiphenyl (2.0 g, 8.6 mmol) was added. The reaction mixture was refluxed for 2 h and cooled to 0° C. on an icebath. Ethyleneoxide (14.0 g, 0.32 mol) was was added. The reaction mixture was refluxed for 18 h, cooled to 0° C. and a saturated solution of ammonium chloride (100 ml) was dropwise added at this temperature. The reaction mixture was diluted with diethyl ether (100 ml) and concentrated hydrochloric acid was added until pH 2. The organic phase was separated, dried (MgSO4) and concentrated in vacuo. The residue was submitted to column chromatography on silica gel (800 ml) using heptane and ethyl acetate (7:3) as eluent to give 8.5 g of 2-(biphenyl-2-yl)ethanol as an oil.
Workup
- temperatureThe reaction mixture was refluxed for 18 h
- temperatureThe reaction mixture was refluxed for 2 h
- temperatureThe reaction mixture was refluxed for 18 h
- temperaturecooled to 0° C.
- additionwas added until pH 2
- customThe organic phase was separated
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-3dc860761bbc47edbfcf113b2754556b
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05604242
Reaction notes
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