Ethanol → [2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5-methyloxazol-4-yl]-acetic acid ethyl ester

HRID 2396074Notes

Reaction equation

HRID 2396074 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[O:17][C:18]([CH3:25])=[C:19]([CH2:21][C:22]([OH:24])=[O:23])[N:20]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[CH3:26][CH2:27]O.S(=O)(=O)(O)O>O>[CH2:26]([O:23][C:22](=[O:24])[CH2:21][C:19]1[N:20]=[C:16]([C:7]2[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=2)[O:17][C:18]=1[CH3:25])[CH3:27]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 135422986HCID 135422986, compound

Product 1

HCID 135725057[2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5-methyloxazol-4-yl]-acetic acid ethyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of [2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyloxazol-4-yl]-acetic acid (1.5 g, 4.35 mmol), EtOH (50 mL), and concentrated sulfuric acid (0.5 mL) was refluxed for 10 hours. The mixture poured into water, and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and crystallization from ethyl ether/hexane gave a light brown solid (1.35g, 83% yield), m.p. 103°-105° C.

Workup

  1. temperaturewas refluxed for 10 hours
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customEvaporation and crystallization from ethyl ether/hexane

Sources & evidence

ORD record
ord-9e41e6b766cc4a639d670d8892141877
Source dataset
uspto-grants-1996_02
Patent number
US05491159

Reaction notes

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