Phenol → Phenyl 2-(4-methylphenyl)-1,3-benzoxazole-5-carboxylate

HRID 426453Notes

Reaction equation

HRID 426453 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17](Cl)=[O:18])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:20]1(O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-:27].[Na+]>C(Cl)Cl.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]([O:18][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:27])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 203909272-(4-Methylphenyl)-1,3-benzoxazole-5-carbonyl chloride

Product 1

HCID 20390931Phenyl 2-(4-methylphenyl)-1,3-benzoxazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution containing 4.43 g. (0.016 mole) of 2-(4-methylphenyl)-5-benzoxazolecarbonyl chloride in 50 ml. of methylene chloride was added dropwise to a solution containing 1.88 g. (0.02 mole) of phenol and 0.80 g. (0.02 mole) of sodium hydroxide in 25 ml. of water. After stirring at 50° for 20 hours, the layers were separated and the organic layer was dried (MgSO4) and concentrated to give 2.9 g. (54%) of ld: UV (CH2Cl2) λmax 306 nm (18,200), ε325 =3500.

Workup

  1. additionA solution containing 4.43 g
  2. additioncontaining 1.88 g
  3. customthe layers were separated
  4. dry with materialthe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customto give 2.9 g

Sources & evidence

ORD record
ord-142236d7dd164d289ccb7f65e6577e66
Source dataset
uspto-grants-1979_10
Patent number
US04169837

Reaction notes

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