Diethyl Ether → HCID 12533728, compound

HRID 1065511Notes

Reaction equation

HRID 1065511 reaction equation
[CH2:1]=[C:2]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][C:6](=[O:14])[CH2:5][C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]1=2.[CH3:19]COCC>>[OH:14][C:6]1([CH3:19])[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:2](=[CH2:1])[C:3]2[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=2[CH2:5]1

Participants

3

Reactant 2

HCID 3283Diethyl EtherHCID 12533720HCID 12533720, compound

Product 1

HCID 12533728HCID 12533728, compound

Procedure

Upon completion of the addition, the mixture was heated at reflux for one hour, then cooled to room temperature. A solution of 15.1 g. (0.065 mole) of 12-methylene-6-oxo-5,6,7,12-tetrahydrodibenzo[a,d]cyclooctene in 100 ml. of ether was added over 5 minutes to the stirred Grignard solution, and the resulting mixture was stirred for one hour at room temperature and quenched in 1 liter of ice water containing 5 g. of ammonium chloride. The resulting suspension was extracted three times with ether (200 ml.), and the combined ether layers were washed once with dilute aqueous sodium bisulfite, once with dilute sodium bicarbonate, and twice with water. The washed ether solution was dried over potassium carbonate, filtered, and evaporated in vacuo to give 6-hydroxy-6-methyl-12-methylene-5,6,7,12-tetrahydrodibenzo[a,d]cyclooctene as a colorless oil, 17.7 g.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux for one hour
  4. customquenched in 1 liter of ice water containing 5 g
  5. extractionThe resulting suspension was extracted three times with ether (200 ml.)
  6. washthe combined ether layers were washed once with dilute aqueous sodium bisulfite, once with dilute sodium bicarbonate
  7. dry with materialThe washed ether solution was dried over potassium carbonate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-6b29c28afd754e188e9637945a159dc2
Source dataset
uspto-grants-1982_05
Patent number
US04329465

Reaction notes

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