Water → HCID 13540113, compound

HRID 648026Notes

Reaction equation

HRID 648026 reaction equation
C([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:9]2[S:10][CH:11]=[C:12]([CH3:13])[C:8]=2[CH:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[OH:3][CH2:4][C:6]1[CH:15]=[CH:14][C:9]2[S:10][CH:11]=[C:12]([CH3:13])[C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13540112HCID 13540112, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 13540113HCID 13540113, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3-methylbenzo[b]thiophene-5-carboxylic acid ethyl ester (14.44 g.) in dry ether (50 ml.) was added dropwise with stirring to a mixture of lithium aluminium hydride (5.32 g.) in dry ether (450 ml.) under an atmosphere of dry nitrogen. Sufficient heat was applied during the addition to maintain gentle reflux. The mixture was heated under reflux with stirring for 3 hours and then cooled. The excess of lithium aluminium hydride was decomposed by the cautious addition with stirring of water (5.3 ml.) followed by 5 N sodium hydroxide solution (5.3 ml.) and finally more water (16 ml.). The mixture was filtered and the filtrate was dried (Na2SO4) and evaporated to give an oil which crystallized on standing. The solid was crystallized from ether/petrol (b.p. 40°-60°) to give 5-hydroxymethyl-3-methylbenzo[b]thiophene (8.93 g.), m.p. 51°-53°.

Workup

  1. temperatureSufficient heat
  2. additionwas applied during the addition
  3. temperatureto maintain gentle reflux
  4. temperatureThe mixture was heated
  5. temperatureunder reflux
  6. temperaturecooled
  7. filtrationThe mixture was filtered
  8. dry with materialthe filtrate was dried (Na2SO4)
  9. customevaporated
  10. customto give an oil which
  11. customcrystallized
  12. customThe solid was crystallized from ether/petrol (b.p. 40°-60°)

Sources & evidence

ORD record
ord-56b455af580f4d4bbff169fe70cc28af
Source dataset
uspto-grants-1983_10
Patent number
US04410539

Reaction notes

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