Hydrochloric Acid → benzo[b]thiophen-2-yl-benzaldehyde

HRID 916854Notes

Reaction equation

HRID 916854 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH:13]=1.Cl.Cl.O.O1CCCC1>CO>[S:16]1[C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:2]=[O:1])=[CH:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21885828Hydrate;hydrochlorideHCID 69436267HCID 69436267, compound

Product 1

HCID 4137517benzo[b]thiophen-2-yl-benzaldehyde

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

For example, the 2-(2-[1,3]dioxolan-2-yl-phenyl) benzo[b]thiophene (3) product is treated with a suitable acid, such as a hydrochloric acid, preferably an aqueous acid, such as a hydrochloric acid/water mixture. The reaction is carried out in a suitable organic solvent such as tetrahydrofuran or methanol. The reaction is heated to reflux for a period of time ranging from about 20 minutes to about 6 hours. The reaction is then quenched with a weak base such as, for example, sodium bicarbonate. The solvent is removed and the resulting mixture may be extracted, concentrated and purified according to techniques well known in the art, to provide benzo[b]thiophen-2-yl-benzaldehyde (4).

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux for a period of time
  3. waitranging from about 20 minutes to about 6 hours
  4. customThe reaction is then quenched with a weak base such as, for example, sodium bicarbonate
  5. customThe solvent is removed
  6. extractionthe resulting mixture may be extracted
  7. concentrationconcentrated
  8. custompurified

Sources & evidence

ORD record
ord-f5f906bc28f54bb2a608c87c581195b8
Source dataset
uspto-grants-2007_09
Patent number
US07271264B2

Reaction notes

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