Water → 2-Benzyloxymethyl-2-cyclohexylpropan-1,3-diol

HRID 704153Notes

Reaction equation

HRID 704153 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)([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-].O.S(=O)(=O)(O)O>CCOCC>[CH2:1]([O:8][CH2:9][C:10]([CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)([CH2:11][OH:12])[CH2:16][OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 19373401Diethyl 2-benzyloxymethyl-2-cyclohexylmalonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 193733732-Benzyloxymethyl-2-cyclohexylpropan-1,3-diol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Diethyl 2-benzyloxymethyl-2-cyclohexyl-malonate (2 g.) was added to a suspension of lithium aluminium hydride (0.63 g.) in dry ether (30 ml), at 0°, under nitrogen. The mixture was stirred at room temperature for twelve hours. Water (5 ml) was added carefully and the mixture was stirred for ten minutes. 10% sulphuric acid solution (10 ml) was added and the mixture was extracted with ether. The ether extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by chromatography on silica, eluting with 1:1 ether:hexane. 2-Benzyloxymethyl-2-cyclohexyl-propan-1,3-diol was obtained as a colourless oil (1.0 g.).

Workup

  1. stirringthe mixture was stirred for ten minutes
  2. extractionthe mixture was extracted with ether
  3. washThe ether extracts were washed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on silica
  7. washeluting with 1:1 ether

Sources & evidence

ORD record
ord-1e3d838fdf9b4f8fbf3ff89bf9f90d75
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Reaction notes

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