Chloroform → 13149-04-7

HRID 2082192Notes

Reaction equation

HRID 2082192 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH:10]=[CH:9][CH2:8][C@H:7]1[C:12](OCC)=[O:13])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.CCCCCC.C(Cl)(Cl)Cl>O1CCCC1>[OH:3][CH2:4][C@H:6]1[C@H:7]([CH2:12][OH:13])[CH2:8][CH:9]=[CH:10][CH2:11]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 12358152Diethyl (1R,2R)-cyclohex-4-ene-1,2-dicarboxylateHCID 21226445Aluminium lithium hydrideHCID 21584099Diethylether hexane

Product 1

HCID 1105176013149-04-7Yield 127.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 25 g of trans-4-cyclohexene-1,2-dicarboxylic acid diethyl ester 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/Hg and at 150° C. in a bulb tube. In this way, 20 g of trans-1,6-dihydroxymethyl-3-cyclohexene is obtained as a colorless oil.

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/Hg and at 150° C. in a bulb tube

Sources & evidence

ORD record
ord-fe329a9fd14842c0b7192036058f5c2d
Source dataset
uspto-grants-1993_02
Patent number
US05187286

Reaction notes

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