Sodium Sulfate → Trans-4,5-bis(hydroxymethyl)-1,2-dimethylcyclohex-1-ene

HRID 1080927Notes

Reaction equation

HRID 1080927 reaction equation
[Li].[CH3:2][C:3]1[CH2:8][C@@H:7]([C:9](OC)=[O:10])[C@H:6]([C:13](OC)=[O:14])[CH2:5][C:4]=1[CH3:17].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[OH:10][CH2:9][C@H:7]1[C@H:6]([CH2:13][OH:14])[CH2:5][C:4]([CH3:17])=[C:3]([CH3:2])[CH2:8]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 2767837dimethyl (1R,2R)-4,5-dimethyl-4-cyclohexene-1,2-dicarboxylateHCID 3028194Lithium

Product 1

HCID 15278040Trans-4,5-bis(hydroxymethyl)-1,2-dimethylcyclohex-1-eneYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium alumium hydride (1.529 g, 0.04 mol) in dry THF (60 ml) at 0° C. was added trans-dimethyl 1,2-dimethylcyclohex-1-ene-4,5-dicarboxylate (2.269 g, 0.01 mol) in dry THF (40 ml) over 30 min. The resultant suspension was stirred for another hour at 0° C., and then saturated sodium sulphate solution (5ml) was added dropwise. The solution was filtered and the filtrate evaporated to give an oil, which on purification gave the title compound in 36% yield. N.m.r: δH (90 MHz, CDCl3) 3.70 (m,4H), 3.55 (bs,2H), 2.02 (m,4H), 1.96 (m,2H), 1.64 ppm (s,6H).

Workup

  1. filtrationThe solution was filtered
  2. customthe filtrate evaporated
  3. customto give an oil, which
  4. customon purification

Sources & evidence

ORD record
ord-1600bd0122724bf782475cb4c5602082
Source dataset
uspto-grants-1996_12
Patent number
US05583261

Reaction notes

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