Benzotrichloride → Trimethyl orthobeznoate

HRID 1439446Notes

Reaction equation

HRID 1439446 reaction equation
ClC(C1C=CC=CC=1)(Cl)Cl.C[O-].[Na+].C[C@@H]1[C@H](O)[C@]2(O)[C@H]([C@:18]34[O:38][C:36]5([C:39]6[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=6)[O:37][C@:21](C(C)=C)([C@H:22]([O:35]5)[C@@H]3[C@@H]3O[C@]3(CO)[C@H]2O)C[C@H]4C)C1>>[CH3:21][O:37][C:36]([O:35][CH3:22])([O:38][CH3:18])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

4

Reactant 3

HCID 7367BenzotrichlorideHCID 10942334Sodium MethoxideHCID 73348815HCID 73348815, compound

Product 1

HCID 69720Trimethyl orthobeznoateYield 51%

Procedure

Methyl orthobenzoate is prepared by reacting one mole of trichloromethylbenzene with 3.15 moles of sodium methylate in methanolic solution for 20 hours at reflux. After filtration and rectification almost pure methyl orthobenzoate is obtained in a yield of 51%. The orthobenzoate has a boiling point at 15-16 torr of 102°-103° C, and nD25 of 1.4858, and contains 0.8% Cl.

Workup

  1. customfor 20 hours
  2. temperatureat reflux
  3. filtrationAfter filtration and rectification almost pure methyl orthobenzoate
  4. customis obtained in a yield of 51%
  5. customat 15-16 torr of 102°-103° C, and nD25 of 1.4858

Sources & evidence

ORD record
ord-d491d7634cca4b55bc718da0c88b51fc
Source dataset
uspto-grants-1977_11
Patent number
US04059656

Reaction notes

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