p-Toluenesulfonic acid → HCID 20432292, compound

HRID 444236Notes

Reaction equation

HRID 444236 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:10]3=[CH:12][CH2:13][CH2:14][CH2:15][C:9]3=[C:8]([CH3:16])[C:7]([CH3:18])(O)[C:6]=2[CH:19]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([CH3:16])=[C:7]([CH3:18])[C:6]=2[CH:19]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 70479913HCID 70479913, compound

Product 1

HCID 20432292HCID 20432292, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

319 g (1 mol) of 8-bromo-10,11-dimethyl-dihydrodibenz[b,f]oxepin-10-ol (crude product) and 1.5 g of p-toluenesulfonic acid are heated in a distillation apparatus under 11 mm Hg for 1 hour at an external temperature of 180° and for 5 hours at an external temperature of 200°, water being eliminated. The distillation receiver is then changed and the 2-bromo-10,11-dimethyldibenz[b,f]oxepine formed is then distilled under a high vacuum; boiling point 142°-148°/0.01 mm Hg. The pale yellow distillate is dissolved in 300 ml of acetonitrile and the solution is cooled to 0°, whereupon the product crystallises out; melting point 117°-119°.

Sources & evidence

ORD record
ord-31a76381d14540839cedc4b47c711ab8
Source dataset
uspto-grants-1981_04
Patent number
US04263315

Reaction notes

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