Oxalyl chloride → HCID 22750665, compound

HRID 1606129Notes

Reaction equation

HRID 1606129 reaction equation
[C:1]([C:4]1[C:14]2[CH2:13][CH2:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([OH:3])=O.[C:20](Cl)(=O)C(Cl)=O>C1C=CC=CC=1>[C:1]([C:4]1[C:14]2[CH2:13][CH2:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:20]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 12525895HCID 12525895, compound

Product 1

HCID 22750665HCID 22750665, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

25 g. of 1-carboxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one in 250 ml. of benzene are heated with 20 g. of oxalyl chloride for 2 hours at reflux and subsequently concentrated under reduced pressure. The resulting crystalline 1-chlorocarbonyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one is dissolved in 200 ml. of benzene and then it is added dropwise to a solution of the magnesium salt of diethyl malonate (about 50 g. in 500 ml. of ether) over a period of about 5 minutes and heated at reflux for 12 hours. Subsequently, the reaction mixture is divided between ether and dilute sulfuric acid, washed with water, sodium bicarbonate solution and water, dried and evaporated. The residue is heated in 30 ml. of ethyl acetate, 20 ml. of water and 3.7 ml. of concentrated sulfuric acid at reflux for 15 hours. Then, it is poured over ice water and extracted with ether. The ethereal extract is washed with water, sodium bicarbonate solution and water, dried and evaporated, whereby 1-acetyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one having a melting point of 65°-68°C. is obtained.

Workup

  1. concentrationsubsequently concentrated under reduced pressure
  2. dissolutionThe resulting crystalline 1-chlorocarbonyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one is dissolved in 200 ml
  3. additionof benzene and then it is added dropwise to a solution of the magnesium salt of diethyl malonate (about 50 g. in 500 ml. of ether) over a period of about 5 minutes
  4. temperatureheated
  5. temperatureat reflux for 12 hours
  6. washwashed with water, sodium bicarbonate solution and water
  7. customdried
  8. customevaporated
  9. temperatureThe residue is heated in 30 ml
  10. temperatureof concentrated sulfuric acid at reflux for 15 hours
  11. additionThen, it is poured over ice water
  12. extractionextracted with ether
  13. extractionThe ethereal extract
  14. washis washed with water, sodium bicarbonate solution and water
  15. customdried
  16. customevaporated

Sources & evidence

ORD record
ord-2399d135fecc498aa31227b5b34e691d
Source dataset
uspto-grants-1976_04
Patent number
US03952017

Reaction notes

Loading…