2,4-Dihydroxybenzaldehyde → HCID 10537643, compound

HRID 1955154Notes

Reaction equation

HRID 1955154 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Cl[CH2:14][C:15]1[CH:19]=[CH:18][S:17][CH:16]=1>CN(C)C=O>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:14][C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 24758Sodium hydrideHCID 124874623-(Chloromethyl)thiophene

Product 1

HCID 10537643HCID 10537643, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

A stirred solution of 2,4-dihydroxybenzaldehyde (31.8 g) in dry dimethylformamide (150 ml) at ambient temperature was treated with sodium hydride (11.96 g; 60% dispersion in mineral oil), portionwise, during 30 minutes. After a further period of 15 minutes, the mixture was treated, dropwise, with a solution of 3-chloromethylthiophene (35 g) in dimethylformamide (50 ml). The mixture was stirred at 70° C. for 2 hours, cooled and the solvent evaporated. The residue was partitioned between ethyl acetate (200 ml) and 0.5 N hydrochloric acid (200 ml) and the aqueous layer was extracted twice with ethyl acetate (100 ml). The combined organic phases were washed with brine (100 ml), dried over magnesium sulphate, and evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:4, v/v), to give a colourless oil, which crystallised on standing. This solid was recrystallized from diisopropyl ether, to give the title compound (8 g) as a white solid.

Workup

  1. waitAfter a further period of 15 minutes
  2. additionthe mixture was treated
  3. temperaturecooled
  4. customthe solvent evaporated
  5. customThe residue was partitioned between ethyl acetate (200 ml) and 0.5 N hydrochloric acid (200 ml)
  6. extractionthe aqueous layer was extracted twice with ethyl acetate (100 ml)
  7. washThe combined organic phases were washed with brine (100 ml)
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:4, v/v)
  11. customto give a colourless oil, which
  12. customcrystallised
  13. customThis solid was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-f0f6838ad0434665b59dbe3bdc29f8b9
Source dataset
uspto-grants-2000_09
Patent number
US06124343

Reaction notes

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