Water → HCID 12874107, compound

HRID 2286838Notes

Reaction equation

HRID 2286838 reaction equation
C(O)(C)C.O.[Cl:6][C:7]1[S:8][CH:9]=[C:10]([CH:13]=[O:14])[C:11]=1[Cl:12].[BH4-].[Na+]>ClCCl>[Cl:6][C:7]1[S:8][CH:9]=[C:10]([CH2:13][OH:14])[C:11]=1[Cl:12]

Participants

6

Reactant 4

HCID 962Water2×HCID 3776IsopropanolHCID 8188164,5-dichlorothiophene-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12874107HCID 12874107, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

300 ml of isopropanol, 300 ml of water and 200 g of 2,3-dichlorothiophene-4-aldehyde are placed in a 2 liter flask; over a period of 45 minutes, 16 g of sodium borohydride is added in portions. The reaction is exothermic and is cooled to take place at from 35° to 40° C. Subsequently, the two-phase mixture is stirred for 30 minutes at this temperature and then 300 ml of water and 500 ml of dichloromethane are added. After the phases have been separated, the aqueous phase is extracted twice with 250 ml of dichloromethane. The organic phases are washed with 250 ml of water and concentrated. The oily residue is taken up in cyclohexane; there is obtained 182 g (87.3% of theory) of crystalline 2,3-dichloro-4-hydroxymethylthiophene, m.p.: 63° to 65° C.

Workup

  1. temperatureis cooled
  2. customat from 35° to 40° C
  3. customAfter the phases have been separated
  4. extractionthe aqueous phase is extracted twice with 250 ml of dichloromethane
  5. washThe organic phases are washed with 250 ml of water
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-82781586b9fa45bf9d58fa24ee1e69db
Source dataset
uspto-grants-1981_05
Patent number
US04268506

Reaction notes

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