Water → 2-(4-Methylphenyl)-4,5-dihydrothiophene-3-carbaldehyde

HRID 1708417Notes

Reaction equation

HRID 1708417 reaction equation
Cl[C:2](=[C:5](CCCl)[C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[CH:3]=[O:4].[S-2:16].[Na+].[Na+].[CH2:19]1[CH2:23]OCC1.O>CCOCC>[CH3:12][C:9]1[CH:8]=[CH:7][C:6]([C:5]2[S:16][CH2:23][CH2:19][C:2]=2[CH:3]=[O:4])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14804Sodium Sulfide2×HCID 54567714HCID 54567714, compound

Product 1

HCID 200928382-(4-Methylphenyl)-4,5-dihydrothiophene-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

15.9 g of α-chloro-β-(2-chloroethyl)-4-methylcinnamaldehyde, prepared in B), and 22 g of sodium sulphide (9 H2O) are added to 200 ml of THF. A sufficient amount of water is added for the sodium sulphide to pass completely into solution, and the mixture is then heated to reflux for 3 hours, cooled and thereafter taken up with ether. The organic phase is separated after settling has taken place, washed with water, then dried over magnesium sulphate and evaporated under vacuum to give 13.5 g of 2-(4'methylphenyl)-4,5-dihydro-3-thiophenecarbaldehyde in the form of an oil which is used without further purification for the next step.

Workup

  1. temperaturethe mixture is then heated
  2. temperatureto reflux for 3 hours
  3. temperaturecooled
  4. customThe organic phase is separated after settling
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-a7f30488fc73406e8c30a6f865463a1b
Source dataset
uspto-grants-1994_10
Patent number
US05358950

Reaction notes

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