Ethylene Oxide → HCID 19046535, compound

HRID 1781452Notes

Reaction equation

HRID 1781452 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1Br)([CH3:3])[CH3:2].[CH2:14]1[O:16][CH2:15]1.[NH4+].[Cl-]>CCOCC>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[CH:15]([OH:16])[CH3:14])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 25517Ammonium ChlorideHCID 121409152-Bromo-1,3-diisopropylbenzene

Product 1

HCID 19046535HCID 19046535, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2,6 diisopropylbromobenzene (see J. Org. Chem., 42(14):2426-2431 (1977) for preparation) (30 g, 124.4 mmol) was added to a suspension of Li powder (1.9 g, 273.6 mmol) in ether (100 nIL) heated under reflux, the heating was continued for another 4 hours, cooled, and the mixture was poured into ethylene oxide which was precooled to -78° C. The mixture was warmed slowly to room temperature, saturated NH4Cl solution was added slowly with caution, the ether layer was separated and washed with brine, dried over MgSO4, filtered, and the solvent was evaporated to dryness. After column chromatography (3:1 hexane:ethyl acetate) pure 2,6-diisopropylphenylethanol was obtained (17 g, 66.3%); NMR (CDCl3):δ 1.2-1.3 (m, 12H), 3.05 (t, 3.15-3.35 (m, 2H), 3.7-3.8 (t, 2H), 7.1-7.3 (m, 3H) ppm.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperaturecooled
  4. customwas precooled to -78° C
  5. customthe ether layer was separated
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-da8af5adbeb644219123efaf215caaa5
Source dataset
uspto-grants-1997_05
Patent number
US05633287

Reaction notes

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