Sodium Hydroxide → HCID 13066737, compound

HRID 1902748Notes

Reaction equation

HRID 1902748 reaction equation
[CH2:1]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[O:25][C:26]([O:35][CH2:36][CH3:37])=[C:27]([CH2:29][C:30]([O:32]CC)=[O:31])[N:28]=2)=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH-].[Na+]>CO.O>[CH2:1]([O:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[O:25][C:26]([O:35][CH2:36][CH3:37])=[C:27]([CH2:29][C:30]([OH:32])=[O:31])[N:28]=2)=[CH:22][CH:23]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12852819HCID 12852819, compound

Product 1

HCID 13066737HCID 13066737, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 20 g of ethyl 2-(4-hexadecyloxyphenyl)-5-ethoxy-4-oxazoleacetate in 200 ml of methanol was added a solution of 7.6 g of sodium hydroxide in 20 ml of water under stirring at room temperature and stirred for about 3.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water and the solution was acidified with hydrochloric acid to pH 1 under cooling. The precipitate was filtered off, dried and recrystallized from methanol to give 11.7 g of the title compound of white powder, m.p. 89°-91° C.

Workup

  1. stirringstirred for about 3.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. temperatureunder cooling
  5. filtrationThe precipitate was filtered off
  6. customdried
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-30fffe9893cc4f69a1557401680004e8
Source dataset
uspto-grants-1982_12
Patent number
US04365066

Reaction notes

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