Hydrochloric Acid → HCID 22915086, compound

HRID 234215Notes

Reaction equation

HRID 234215 reaction equation
[C:1]([O:20][CH2:21][CH2:22][CH2:23][CH:24]=[O:25])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:27].[K+].Cl.S(=O)(O)[O-].[Na+]>CC(C)=O.O>[C:1]([O:20][CH2:21][CH2:22][CH2:23][C:24]([OH:27])=[O:25])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 516875Potassium PermanganateHCID 11078038HCID 11078038, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 22915086HCID 22915086, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 56.2 g of 4-trityloxy-butanal in 430 ml of acetone and 170 ml of water were added portionwise over 1.5 h 27.0 g of potassium permanganate, the temperature of the mixture being maintained at 20° to 25° C. Stirring was continued for 3 h, and then, the pH of the mixture was set to 5 by addition of 22 ml of 3N hydrochloric acid. Over 30 min, 300 ml of 38% sodium bisulfite solution were added dropwise at a reaction temperature of 20° to 30° C. The pH was lowered to 2 by addition of 80 ml of 3N hydrochloric acid, and subsequently the mixture was extracted with 1 l of ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and the solvent was evaporated in vacuo. The residue was crystallized from ethyl acetate/hexane to yield 46.0 g of 4-trityloxy-butyric acid as a white solid of m.p. 137°-140° C.

Workup

  1. temperaturethe temperature of the mixture being maintained at 20° to 25° C
  2. waitOver 30 min
  3. extractionsubsequently the mixture was extracted with 1 l of ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-89b9e90ef43b44fa85f67b5c97edb7b1
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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