Hydrochloric Acid → [4-(1,3-Benzoxazol-2-yl)phenyl](2-hydroxy-4-methoxyphenyl)methanone

HRID 1288413Notes

Reaction equation

HRID 1288413 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=1.ClC(Cl)C.Cl>ClCCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:18]=[CH:17][C:13]([C:14]([C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][C:27]=2[OH:31])=[O:15])=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 63651,1-DichloroethaneHCID 90073-MethoxyphenolHCID 6451240Aluminum(III) ChlorideHCID 20556623HCID 20556623, compound

Product 1

HCID 21501898[4-(1,3-Benzoxazol-2-yl)phenyl](2-hydroxy-4-methoxyphenyl)methanoneYield 61%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
10 °C

Procedure

To a stirred solution of 12.8 g. (0.05 mole) of 4-(2-benzoxazolyl)benzoyl chloride in 200 ml. of 1,2-dichloroethane is added, in small increments, 14.8 g. (0.11 mole) of anhydrous alumimum chloride at room temperature. The resulting solution is cooled to 10° C. and a solution of 6.2 g. (0.05 mole) of m-methoxyphenol in 50 ml. of dichloroethane is added dropwise over a period of 10 min. The reaction mixture is stirred at 10° C. for 30 min., then allowed to warm to room temperature and stirred at reflux for 1 hr. The reaction mixture is cooled to room temperature and combined with 300 g. cracked ice containing 50 ml. of concentrated hydrochloric acid. The organic layer is separated and washed 2 times with warm water. The organic layer is filtered through filter-cel and the solvent is evaporated on a steam bath leaving a yellow solid residue. The crude solid product is recrystallized from toluene to give 10 g. yellow crystals, m.p. 177°-179° C. (61% yield). The structure and purity of the product are confirmed by IR, NMR, and elemental analysis.

Workup

  1. customat room temperature
  2. temperatureto warm to room temperature
  3. stirringstirred
  4. temperatureat reflux for 1 hr
  5. temperatureThe reaction mixture is cooled to room temperature
  6. customThe organic layer is separated
  7. washwashed 2 times with warm water
  8. filtrationThe organic layer is filtered
  9. filtrationthrough filter-cel
  10. customthe solvent is evaporated on a steam bath
  11. customleaving a yellow solid residue
  12. customThe crude solid product is recrystallized from toluene
  13. customto give 10 g

Sources & evidence

ORD record
ord-d27c7cf4f3bc4f81be949ddaf6f05fa7
Source dataset
uspto-grants-1976_10
Patent number
US03988295

Reaction notes

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