Acetic Acid → 4-(2-Decyl-1,3-thiazol-5-yl)phenol

HRID 234568Notes

Reaction equation

HRID 234568 reaction equation
[CH2:1]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)=[CH:14][N:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(O)(=O)C.Br>O>[CH2:1]([C:11]1[S:12][C:13]([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)=[CH:14][N:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 23354792HCID 23354792, compound

Product 1

HCID 233547574-(2-Decyl-1,3-thiazol-5-yl)phenolYield 63.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Then, in a 500 ml-three-necked flask, 11.6 g (35.0 mM) of 2-decyl-5-(4-methoxyphenyl)tiazole, 93 ml of acetic acid and 102 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 benzene. The organic layer was successively washed with water, 5%-sodium hydrogenecarbonate aqueous solution and water, followed by distilling-off of the solvent under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform) and recrystallized from toluene to obtain 7.0 g of 2-decyl-5-(4-hydroxyphenyl )thiazole (Yield: 63.1%).

Workup

  1. customAfter the reaction
  2. additionthe reaction mixture was poured
  3. extractionfollowed by extraction with benzene
  4. washThe organic layer was successively washed with water, 5%-sodium hydrogenecarbonate aqueous solution and water
  5. customThe residue was purified by silica gel column chromatography (eluent: chloroform)
  6. customrecrystallized from toluene

Sources & evidence

ORD record
ord-c83e2afa4fa44455aa40ec4c59c15ebc
Source dataset
uspto-grants-1997_01
Patent number
US05595685

Reaction notes

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