Potassium Hydroxide → HCID 18992152, compound

HRID 375741Notes

Reaction equation

HRID 375741 reaction equation
[CH3:1][C:2]([CH3:28])([CH2:7][O:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5]C)=[O:4].[OH-].[K+]>C(O)CO.C(OCC)(=O)C>[CH3:1][C:2]([CH3:28])([CH2:7][O:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 18992038HCID 18992038, compound

Product 1

HCID 18992152HCID 18992152, compoundYield 14.6%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 53.5 g of raw methyl 2,2-dimethyl-3-trityloxy-propionate and 16.8 g of potassium hydroxide in 100 ml of ethylene glycol was heated to 160° C. for 4 hours. The mixture was cooled, diluted with 400 ml of ethyl acetate, and then washed successively with ice-cold 1N hydrochloric acid and with brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated in vacuo. The residue was triturated with diethylether, unsoluble material was filtered off, and the filtrate was evaporated. Crystallization of the residue from diethylether/hexane provided 7.5 g of 2,2-dimethyl-3-trityloxy-propanoic acid, m.p. 153°-158° C.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed successively with ice-cold 1N hydrochloric acid and with brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was triturated with diethylether, unsoluble material
  6. filtrationwas filtered off
  7. customthe filtrate was evaporated
  8. customCrystallization of the residue from diethylether/hexane

Sources & evidence

ORD record
ord-3ef899c094724e51945e9f411b5b8279
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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