p-Toluenesulfonic acid monohydrate → HCID 22261431, compound

HRID 1610688Notes

Reaction equation

HRID 1610688 reaction equation
[Br:1][C:2]1[C:7]2[CH:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][C:6]=2[C:5]([CH3:14])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:7]2[CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][C:6]=2[C:5]([CH3:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22261561HCID 22261561, compound

Product 1

HCID 22261431HCID 22261431, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-bromo-1-methyl-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ol (6.213 g, 24.35 mmol) and p-toluenesulfonic acid monohydrate (0.46 g, 2.44 mmol) in toluene (100 ml) was heated under reflux in a reaction vessel equipped with a Dean-Stark trap under dehydrating conditions for 0.5 hr. After the reaction solution was cooled to room temperature, the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane) to give the objective substance.

Workup

  1. temperatureunder reflux in a reaction vessel
  2. customequipped with a Dean-Stark trap under dehydrating conditions for 0.5 hr
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography (hexane)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-8f1e735b83a14aa18f7b3e442f4e531b
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…