Ethylene Oxide → HCID 19046535, compound

HRID 2396255Notes

Reaction equation

HRID 2396255 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) forpreparation) (30 g, 124.4 mmol) was added to a suspension of Li powder (1.9g, 273.6 mmol) in ether (100 mL) 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, 6.3%); NMR (CDCl3): δ 1.2-1.3 (m, 12H) , 3.05 (t, 2H), 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-1b52d62042e4436f92036ded1c6e39a7
Source dataset
uspto-grants-1996_02
Patent number
US05491172

Reaction notes

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