Hydrochloric Acid → Trimethylolpropane

HRID 1613094Notes

Reaction equation

HRID 1613094 reaction equation
CC1(C)[O:7][CH2:6][C:5]([CH2:10][CH3:11])([CH2:8][OH:9])[CH2:4][O:3]1.Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[K+]>CO>[OH:3][CH2:4][C:5]([CH2:8][OH:9])([CH2:10][CH3:11])[CH2:6][OH:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 14797Potassium HydroxideHCID 118161521,3-Dioxane-5-methanol, 5-ethyl-2,2-dimethyl-

Product 1

HCID 6510TrimethylolpropaneYield 179.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7.8 g (17 mmol) of the crude sulfonate 6 prepared in step 2 are introduced into 60 ml of methanol, and 3 N hydrochloric acid is added dropwise until the pH is less than 5. 400 mg of p-toluenesulfonic acid are subsequently added, the mixture is stirred at room temperature for 21 hours, and methanolic potassium hydroxide solution is added until the mixture is slightly alkaline (pH≈8 to 9). The solvent is removed by distillation in vacuo, and the residue which remains is separated by column chromatography on silica gel using dichloromethane as the eluent, giving 4.1 g of a colorless oil 7.

Workup

  1. additionis added dropwise until the pH is less than 5
  2. customThe solvent is removed by distillation in vacuo
  3. customthe residue which remains is separated by column chromatography on silica gel

Sources & evidence

ORD record
ord-93887c0091264eff95cab08348e34c0f
Source dataset
uspto-grants-1993_03
Patent number
US05191069

Reaction notes

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