Water → 1,2-Dihydroxycyclohexanemethanol

HRID 258792Notes

Reaction equation

HRID 258792 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].S([O-])([O-])(=O)=[O:8].[Mg+2].[C:13]1([CH2:19][OH:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1.[OH2:21]>C(O)C>[OH:21][C:13]1([CH2:19][OH:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[OH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 317542(Cyclohex-1-en-1-yl)methanolHCID 516875Potassium Permanganate

Product 1

HCID 203346281,2-Dihydroxycyclohexanemethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 24.9 g of potassium permanganate and 18.7 g of magnesium sulfate in 498 ml of water was added dropwise during 1.5 hours to a solution of 22.23 g of 1-cyclohexenemethanol in 373 ml of ethanol. During the dropwise addition, the reaction mixture temperature was maintained at 15°-20°. The reaction mixture was filtered to remove the by-product manganese dioxide. The filtrate was evaporated under reduced pressure to a residual oil. The residual oil was taken up in ethanol and dried with magnesium sulfate. The mixture was filtered and the filtrate evaporated under reduced pressure to a residual oil. The residual oil was distilled using a short-path distilling system to give 6.44 g of 1,2-dihydroxycyclohexanemethanol; bp 124°-125°/0.025 mm.

Workup

  1. additionDuring the dropwise addition
  2. temperaturethe reaction mixture temperature was maintained at 15°-20°
  3. filtrationThe reaction mixture was filtered
  4. customto remove the by-product manganese dioxide
  5. customThe filtrate was evaporated under reduced pressure to a residual oil
  6. dry with materialdried with magnesium sulfate
  7. filtrationThe mixture was filtered
  8. customthe filtrate evaporated under reduced pressure to a residual oil
  9. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-bd32446ac2ce41f88dc3702ccd49041a
Source dataset
uspto-grants-1977_07
Patent number
US04035178

Reaction notes

Loading…