Sodium Hydroxide → 2-Benzyloxymethyl-2-(2,2-dimethylpropyl)-propan-1,3-diol

HRID 345373Notes

Reaction equation

HRID 345373 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH2:21][C:22]([CH3:25])([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]([O:8][CH2:9][C:10]([CH2:21][C:22]([CH3:25])([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 15021954Diethyl 2-benzyloxymethyl-2-(2,2-dimethylpropyl)malonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 150219552-Benzyloxymethyl-2-(2,2-dimethylpropyl)-propan-1,3-diol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Diethyl 2-benzyloxymethyl-2-(2,2-dimethylpropyl)malonate (15 g.) in dry diethyl ether (50 ml.) was added slowly to a stirred suspension of lithium aluminium hydride (7.0 g.) in dry diethyl ether (200 ml.) at 0°, under nitrogen. The mixture was stirred at room temperature for 12 hours. Aqueous sodium hydroxide solution (25 ml., 10% solution) was added carefully. The mixture was filtered and the solid was washed with diethyl ether. The filtrates were dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by chromatography on silica, eluting with 1:4 ethyl acetate:hexane. 2-Benzyloxymethyl-2-(2,2-dimethylpropyl)-propan-1,3-diol was obtained as a colourless oil (5.5 g.).

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with diethyl ether
  3. dry with materialThe filtrates were dried over anhydrous magnesium sulphate
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatography on silica
  6. washeluting with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-5902787cd8244e90957e788e7028c453
Source dataset
uspto-grants-1991_10
Patent number
US05057508

Reaction notes

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