Phosphorus oxychloride → HCID 54311106, compound

HRID 1648844Notes

Reaction equation

HRID 1648844 reaction equation
[CH3:1][CH:2]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH:6](O)[CH2:5][C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]1=2.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[CH3:1][CH:2]1[C:3]2[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=2[CH2:5][CH:6]=[CH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12533760HCID 12533760, compound

Product 1

HCID 54311106HCID 54311106, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

12-Methyl-5,6,7,12-tetrahydrodibenzo[a,d]cycloocten-6-ol (2.7 g., 0.011 mole) in 50 ml. of pyridine was treated with 15 ml. of phosphorous oxychloride. The mixture was heated at reflux for 45 minutes, cooled, and poured carefully into 600 ml. of stirred ice water. The resulting mixture was extracted three times with ether, and the combined ether layers were washed once with water, once with 1 N hydrochloric acid, and twice with water. The washed ether solution was dried over potassium carbonate, filtered, and evaporated in vacuo to give 1.9 g. of colorless oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 45 minutes
  3. temperaturecooled
  4. additionpoured carefully into 600 ml
  5. extractionThe resulting mixture was extracted three times with ether
  6. washthe combined ether layers were washed once with water, once with 1 N hydrochloric acid
  7. dry with materialThe washed ether solution was dried over potassium carbonate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto give 1.9 g

Sources & evidence

ORD record
ord-a9a57d6d0ea04d8c8ddb77616fe928e5
Source dataset
uspto-grants-1983_11
Patent number
US04414154

Reaction notes

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