Sodium Hydroxide → 1,2-Dihydroxycyclohexanemethanol

HRID 258793Notes

Reaction equation

HRID 258793 reaction equation
[O:1]1[CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:2]12[CH2:8][OH:9].[OH-:10].[Na+]>S(=O)(=O)(O)O.O1CCOCC1.O>[OH:10][C:2]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[OH:1]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 141075391,2-Epoxycyclohexanemethanol

Product 1

HCID 203346281,2-Dihydroxycyclohexanemethanol

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture of 10.6 g of 1,2-epoxycyclohexanemethanol and 8 drops of concentrated sulfuric acid in 100 ml of p-dioxane and 100 ml of water was heated at 60°-70° for 18 hours. The reaction mixture was neutralized with sodium hydroxide, and evaporated under reduced pressure to a viscous residue. The residue was taken up in methanol and dried with sodium sulfate. The mixture was filtered and the filtrate evaporated under reduced pressure to a residue. The residue was distilled to give 10.8 g of 1,2-dihydroxycyclohexanemethanol; bp 170°-240°/0.02 mm. The nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturewas heated at 60°-70° for 18 hours
  2. customevaporated under reduced pressure to a viscous residue
  3. dry with materialdried with sodium sulfate
  4. filtrationThe mixture was filtered
  5. customthe filtrate evaporated under reduced pressure to a residue
  6. distillationThe residue was distilled

Sources & evidence

ORD record
ord-9fd6a13a7c744b85b3d7e684dcf9e088
Source dataset
uspto-grants-1977_07
Patent number
US04035178

Reaction notes

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