Sodium Hydroxide → 2-Benzylthiomethyl-2-isobutyl-propan-1,3-diol

HRID 704140Notes

Reaction equation

HRID 704140 reaction equation
[CH2:1]([S:8][CH2:9][C:10]([CH2:21][CH:22]([CH3:24])[CH3:23])([C:16](OCC)=[O:17])[C:11](OCC)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C(OCC)C>[CH2:1]([S:8][CH2:9][C:10]([CH2:21][CH:22]([CH3:24])[CH3:23])([CH2:16][OH:17])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 20075597HCID 20075597, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 200755682-Benzylthiomethyl-2-isobutyl-propan-1,3-diol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Diethyl 2-benzylthiomethyl-2-isobutylmalonate (32.0 g.) in dry diethyl ether (60 ml.) was added to a stirred suspension of lithium aluminium hydride (7.0 g.) in dry diethyl ether (400 ml.), at 0°, under nitrogen. The mixture was stirred at room temperature for three hours and then refluxed with stirring for a further three hours. The mixture was cooled and 10% aqueous sodium hydroxide solution (25 ml.) was added very carefully. The mixture was filtered and the solid was washed with ether. The filtrates were dried over anhydrous magnesium sulphate and evaporated in vacuo. 2-Benzylthiomethyl-2-isobutyl-propan-1,3-diol was obtained as a colourless solid (20 g.) and was used without further purification.

Workup

  1. temperaturerefluxed
  2. stirringwith stirring for a further three hours
  3. temperatureThe mixture was cooled
  4. filtrationThe mixture was filtered
  5. washthe solid was washed with ether
  6. dry with materialThe filtrates were dried over anhydrous magnesium sulphate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-d42ee46465c7435fad122ec6bb222dc1
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Reaction notes

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