2,4-Di-tert-butylphenol → HCID 54360737, compound

HRID 2260444Notes

Reaction equation

HRID 2260444 reaction equation
[O-]CC.[Na+].[C:5]([C:9]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[CH:11][C:10]=1[OH:19])([CH3:8])([CH3:7])[CH3:6].[CH:20]12[O:25][CH:21]1[CH2:22][CH2:23][CH2:24]2>C(O)C>[CH3:6][C:5]([C:9]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[CH:11][C:10]=1[O:19][C@@H:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[OH:25])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 73112,4-Di-tert-butylphenolHCID 92446-Oxabicyclo[3.1.0]hexaneHCID 2723922Sodium ethoxide

Product 1

HCID 54360737HCID 54360737, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium ethoxide in ethanol (prepared by dissolving 230 mg of sodium in 25 ml of ethanol) was added 2.06 g (10.0 mmoles) of 2,4-di-t-butylphenol. The mixture was stirred for 5 minutes, and then 841 mg (10.0 mmoles) of cyclopentene oxide was added. After refluxing overnight, the mixture was cooled and evaporated, the residue partitioned between diethyl ether and dilute aqueous hydrochloric acid, the aqueous layer further extracted with ether, the combined organic extracts washed with brine, dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue over silica gel using 10% ethyl acetate-hexane as eluent gave the title compound, 1.25 g, as a white crystalline solid, m.p. 111.5°-112° C.

Workup

  1. temperatureAfter refluxing overnight
  2. temperaturethe mixture was cooled
  3. customevaporated
  4. customthe residue partitioned between diethyl ether and dilute aqueous hydrochloric acid
  5. extractionthe aqueous layer further extracted with ether
  6. washthe combined organic extracts washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-31b22b7d8f80476db436f08e5bca37ee
Source dataset
uspto-grants-1995_12
Patent number
US05476944

Reaction notes

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