Tetrahydrofuran → HCID 18461213, compound

HRID 2303444Notes

Reaction equation

HRID 2303444 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].OC1C=[CH:15][C:11]([C:12](O)=[S:13])=[CH:10]C=1C.[CH2:18]1[CH2:22][O:21][CH2:20][CH2:19]1>>[OH:21][CH2:20][C:19]1[CH:18]=[CH:22][C:12]([SH:13])=[C:11]([CH3:15])[CH:10]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 178427262HCID 178427262, compound

Product 1

HCID 18461213HCID 18461213, compound

Conditions

Temperature
60 °C

Procedure

95% LiAlH4 (0.55 g, 14 mmol) is introduced in absolute THF (10 ml) into a three-necked flask which is heated and flushed with argon. A solution of 4-hydroxy-3-methylthiobenzoic acid (1.37 g; 7.4 mmol) in absolute THF (15 ml) is added dropwise to this initial mixture with ice-cooling in the course of 5 min such that only moderate evolution of gas takes place. After addition is complete, the cooling is removed and the reaction mixture is stirred at RT for 30 min and at 55-65° C. for a further 21 h. After the reaction mixture has cooled to RT, it is treated carefully with ice water with ice-cooling. The basic Al(OH)3 precipitate is dissolved by addition of 10% strength sulfuric acid and the aqueous, acidic solution (pH=1) is extracted with diethyl ether (150 ml). The phenolic product is extracted from the combined ethereal extract using 2 portions of sodium hydroxide solution (10%, 50 ml). The alkaline sodium hydroxide extract is adjusted to pH=7 using hydrochloric acid (20% strength), the precipitate is taken up using diethyl ether (50 ml), and the neutral aqueous solution is extracted with diethyl ether (100 ml). The combined, ethereal extract is washed with saturated NaCl solution, dried over Na2SO4 and concentrated: a crystalline, white residue remains.

Workup

  1. temperatureis heated
  2. customflushed with argon
  3. temperaturecooling in the course of 5 min such that only moderate evolution of gas
  4. additionAfter addition
  5. customthe cooling is removed
  6. temperatureAfter the reaction mixture has cooled to RT
  7. additionit is treated carefully with ice water with ice-
  8. temperaturecooling
  9. dissolutionThe basic Al(OH)3 precipitate is dissolved by addition of 10% strength sulfuric acid
  10. extractionthe aqueous, acidic solution (pH=1) is extracted with diethyl ether (150 ml)
  11. extractionThe phenolic product is extracted from the combined ethereal
  12. extractionextract
  13. extractionThe alkaline sodium hydroxide extract
  14. extractionthe neutral aqueous solution is extracted with diethyl ether (100 ml)
  15. extractionethereal extract
  16. washis washed with saturated NaCl solution
  17. dry with materialdried over Na2SO4
  18. concentrationconcentrated

Sources & evidence

ORD record
ord-4cd0d35a061d486daabad5b56f00e3d9
Source dataset
uspto-grants-2002_08
Patent number
US06432988B1

Reaction notes

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