Acetic Acid → 4-{2-(4-Hexylphenyl)thiazole-5-yl}phenol

HRID 1587266Notes

Reaction equation

HRID 1587266 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=3)=[CH:16][N:17]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(O)(=O)C.Br>O>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=3)=[CH:16][N:17]=2)=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 219971642-(4-Hexylphenyl)-5-(4-methoxyphenyl)-1,3-thiazole

Product 1

HCID 233547624-{2-(4-Hexylphenyl)thiazole-5-yl}phenolYield 75.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 300 ml-three-necked flask, 13.9 g (39.3 mM) of 2-(4-hexylphenyl)-5-(4-methoxyphenyl)1,3-thiazole, 76.5 ml of acetic acid and 69.5 ml of 47%-hydrobromic acid were placed, followed by heat-stirring for 16 hours at 100°-110° C. After the reaction, the reaction mixture was poured into cool water, followed by extraction with ethyl acetate. The organic layer was successively washed with water, 5%-sodium hydrogencarbonate aqueous solution and water, followed by drying and distilling-off of the solvent under reduced pressure. The residue was dissolved in a mixture solvent of ethanol/chloroform =1/1, followed by decolorization with activated carbon and distilling-off of the solvent under reduced pressure. The resultant residue was recrystallized two times from toluene to obtain 10.0 g of 2-(4-hexylphenyl)-5-(4-hydroxyphenyl)-1,3-thiazole (Yield: 75.8%).

Workup

  1. customAfter the reaction
  2. additionthe reaction mixture was poured
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was successively washed with water, 5%-sodium hydrogencarbonate aqueous solution and water
  5. customby drying and distilling-off of the solvent under reduced pressure
  6. dissolutionThe residue was dissolved in a mixture solvent of ethanol/chloroform =1/1
  7. customThe resultant residue was recrystallized two times from toluene

Sources & evidence

ORD record
ord-1345ab6c0dac4ca0b343a20b2c7e410a
Source dataset
uspto-grants-1993_06
Patent number
US05217645

Reaction notes

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