Iodine → HCID 21648789, compound

HRID 870473Notes

Reaction equation

HRID 870473 reaction equation
II.Br[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH3:12].[O:13]1[CH2:15][CH2:14]1>O1CCCC1>[CH2:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:15][CH2:14][OH:13])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 807IodineHCID 6354Ethylene OxideHCID 157489771-bromo-2-propylbenzene

Product 1

HCID 21648789HCID 21648789, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Into a 250-mL 3-necked round-bottom flask, maintained with a nitrogen atmosphere, was placed I2 (10 mg, 0.04 mmol) and Mg (500 mg, 20.83 mmol, 2.07 equiv). Then 1-bromo-2-propylbenzene (2.0 g, 10.05 mmol, 1.00 equiv) dissolved in tetrahydrofuran (50 mL) was added dropwise into the flask and the mixture was heated to reflux. After the reaction was complete the resulting mixture was cooled to 0° C. and then oxirane (50 mL) was added in one portion. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 5 mL of NH4Cl (aq.). The solids were filtered out. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). Purification afforded 0.24 g (15%) of 2-(2-propylphenyl)ethan-1-ol as a colorless oil.

Workup

  1. temperatureInto a 250-mL 3-necked round-bottom flask, maintained with a nitrogen atmosphere
  2. additionwas added dropwise into the flask
  3. temperaturethe mixture was heated to reflux
  4. customThe reaction was then quenched by the addition of 5 mL of NH4Cl (aq.)
  5. filtrationThe solids were filtered out
  6. concentrationThe filtrate was concentrated under vacuum
  7. customPurification

Sources & evidence

ORD record
ord-d5fa3bdbf3694620ad2fc6bde0b47e28
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Reaction notes

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