Chloroform → cis-1,2-Dihydroxymethylcyclohex-4-ene

HRID 2082191Notes

Reaction equation

HRID 2082191 reaction equation
[C@@H:1]12[C:10](=O)[O:9][C:7](=[O:8])[C@@H:2]1[CH2:3][CH:4]=[CH:5][CH2:6]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.O.C(Cl)(Cl)Cl>O1CCCC1>[OH:8][CH2:7][C@H:2]1[C@@H:1]([CH2:10][OH:9])[CH2:6][CH:5]=[CH:4][CH2:3]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 98495Tetrahydrophthalic anhydride, cis-HCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)

Product 1

HCID 11275057cis-1,2-Dihydroxymethylcyclohex-4-eneYield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 25 g of cis-4-cyclohexene-1,2-dicarboxylic acid anhydride in 140 ml of tetrahydrofuran is instilled in a suspension of 10 g of lithium aluminum hydride in 140 ml of tetrahydrofuran at room temperature and the mixture is then stirred for 3 hours at reflux temperature. It is cooled to 0° C. a mixture of tetrahydrofuran/water (1+1) is instilled slowly, stirred for 30 minutes, mixed with 150 ml of chloroform, filtered and the filtrate is concentrated by evaporation in a vacuum. The residue is distilled at 0.2 mm/Torr and 150° C. on a bulb tube. After recrystallization of the distillate from toluene/pentane, 21 g of cis-1,6-dihydroxymethyl-3-cyclohexene is obtained as colorless crystals, melting point 33°-35° C.

Workup

  1. temperatureat reflux temperature
  2. stirringstirred for 30 minutes
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated by evaporation in a vacuum
  5. distillationThe residue is distilled at 0.2 mm/Torr and 150° C. on a bulb tube
  6. customAfter recrystallization of the distillate from toluene/pentane

Sources & evidence

ORD record
ord-1d094435d749402ca67fb1891241d8e7
Source dataset
uspto-grants-1993_02
Patent number
US05187286

Reaction notes

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