Hydrochloric Acid → HCID 14972913, compound

HRID 1633403Notes

Reaction equation

HRID 1633403 reaction equation
N1C=CC=CC=1.O[C:8]([CH:11]1[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH2:12]1)([CH3:10])[CH3:9].P(Cl)(Cl)(Cl)=O.Cl>CCOCC>[C:8](=[C:11]1[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH2:12]1)([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 131713954HCID 131713954, compound

Product 1

HCID 14972913HCID 14972913, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into 30 ml of dried pyridine, was dissolved 1.78 g of 1-(1-hydroxy-1-methylethyl)benzocyclobutene. To the solution, was added dropwise 3.37 g of phosphorus oxychloride over a period of 5 minutes at room temperature. The mixture was stirred for 24 hours at room temperature, then poured into 3% aqueous cold hydrochloric acid solution and admixed with ether. After the ether layer was separated, the aqueous layer was extracted twice with ether. The ether layers were combined, washed with saturated aqueous sodium hydrogencarbonate solution, then with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain as the residue 1.5 g of a mixture of the intended product and 1-isopropenylbenzocyclobutene. This mixture was used without further purification as the starting material in the next step of preparation.

Workup

  1. customAfter the ether layer was separated
  2. extractionthe aqueous layer was extracted twice with ether
  3. washwashed with saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialwith saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-597e550710d94fecb84215deb38c2fe6
Source dataset
uspto-grants-1984_10
Patent number
US04480118

Reaction notes

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