Potassium Carbonate → 2-[4-(5-Chloro-2-benzoxazolyloxy)-phenoxy]-propionyl-glycolic acid methyl ester

HRID 1979654Notes

Reaction equation

HRID 1979654 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([C:6](=[O:17])[CH:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH3:8])[OH:5].C(=O)([O-])[O-].[K+].[K+].Cl[C:26]1[O:27][C:28]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:29]=2[N:30]=1>C(#N)C>[CH3:1][O:2][C:3](=[O:18])[CH:4]([C:6](=[O:17])[CH:7]([O:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:26]2[O:27][C:28]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:29]=3[N:30]=2)=[CH:14][CH:15]=1)[CH3:8])[OH:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 103975782,5-DichlorobenzooxazoleHCID 538031292-(4-Hydroxyphenoxy)-propionyl-glycolic acid methyl ester

Product 1

HCID 541383282-[4-(5-Chloro-2-benzoxazolyloxy)-phenoxy]-propionyl-glycolic acid methyl esterYield 84.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

25.4 g of 2-(4-hydroxyphenoxy)-propionyl-glycolic acid methyl ester and 16.6 g of potassium carbonate in 180 cc of acetonitrile are refluxed for 1 hour to form a salt. After addition of 20 g of 2,5-dichlorobenzoxazole, the mixture is refluxed for 10 hours. The salt is filtered off at 60° C. and the acetonitrile is distilled off. The residue is freed in vacuo from volatile residues. 34 g (84.8% of theory) of 2-[4-(5-chloro-2-benzoxazolyloxy)-phenoxy]-propionyl-glycolic acid methyl ester are obtained as a brownish viscous oil, nD23 =1.5587. ##STR12##

Workup

  1. customto form a salt
  2. temperaturethe mixture is refluxed for 10 hours
  3. filtrationThe salt is filtered off at 60° C.
  4. distillationthe acetonitrile is distilled off

Sources & evidence

ORD record
ord-eb641838f394492891f8b1c028e5fecf
Source dataset
uspto-grants-1984_11
Patent number
US04482373

Reaction notes

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