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

HRID 128769Notes

Reaction equation

HRID 128769 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH2:13][C@@H:12]([C:14](OC)=[O:15])[C@H:11]([C:18](OC)=[O:19])[CH2:10][C:9]=1[CH3:22].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[OH:15][CH2:14][C@H:12]1[C@H:11]([CH2:18][OH:19])[CH2:10][C:9]([CH3:22])=[C:8]([CH3:7])[CH2:13]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 2767837dimethyl (1R,2R)-4,5-dimethyl-4-cyclohexene-1,2-dicarboxylateHCID 21226445Aluminium lithium hydride

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 aluminium hydride (1.52 g, 0.04 mol) in dry THF (60 ml) at 0° C. was added trans-dimethyl 1,2-dimethylcyclohex-1-ene-4,5-dicarboxylate (2.26 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 (5 ml) 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-dace28829ce0405b9422d73e4635c37b
Source dataset
uspto-grants-1995_11
Patent number
US05464873

Reaction notes

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