Pyridinium hydrochloride → HCID 66664001, compound

HRID 2039418Notes

Reaction equation

HRID 2039418 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:14]2[S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:13]=2[CH:12]=[CH:11][CH:10]=1.Cl.[NH+]1C=CC=CC=1>O>[CH:12]1[C:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[S:15][C:14]=2[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[OH:2])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 66663720HCID 66663720, compound

Product 1

HCID 66664001HCID 66664001, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4-(2-Methoxyphenyl)dibenzo[b,d]thiophene (6.6 g, 23 mmol) and pyridinium hydrochloride (27 g, 230 mmol) were mixed together, placed in the 100 ml round bottom flask and heated to reflux for 45 min. Reaction mixture was cooled to 60° C., diluted with 100 ml water and extracted with ethyl acetate. The organic phase was separated, dried over magnesium sulfate, filtered and evaporated. The residue was subjected to column chromatography on silica (eluent hexane/ethyl acetate 5/1), providing 4.00 g of 2-(dibenzo[b,d]thiophen-4-yl)phenol as clear solidified oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 45 min
  3. customReaction mixture
  4. extractionextracted with ethyl acetate
  5. customThe organic phase was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-0a2d6269400a4fe4b91886b2ebe1cc3b
Source dataset
uspto-grants-2013_11
Patent number
US08580402B2

Reaction notes

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