Diethyl chloromalonate → [3-(2-Benzylaminoethyl)-phenoxy]-malonic acid

HRID 2248139Notes

Reaction equation

HRID 2248139 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Cl[CH:22]([C:28]([O:30]CC)=[O:29])[C:23]([O:25]CC)=[O:24]>C(O)C>[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[O:17][CH:22]([C:28]([OH:30])=[O:29])[C:23]([OH:25])=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 84182Diethyl chloromalonateHCID 10942334Sodium MethoxideHCID 198055723-(2-Benzylaminoethyl)-phenol

Product 1

HCID 19805556[3-(2-Benzylaminoethyl)-phenoxy]-malonic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 8.0 g. (35.2 mMol) 3-(2-benzylaminoethyl)-phenol and 100 ml. ethanol there are added 35.2 mMol sodium methylate in the form of a methanolic solution and thereafter 6.8 g. (35.2 mMol) diethyl chloromalonate. After stirring for 4 hours, the reaction mixture is evaporated. 50 ml. Diethyl ether are added to the residue, as well as ice-cold 1N aqueous sodium hydroxide solution, shaken up and the ethereal phase is separated off. After drying over anhydrous sodium sulphate, the sulphate is precipitated from it by the dropwise addition of concentrated sulphuric acid, which is filtered off with suction and washed with diethyl ether. The product is very hygroscopic and is obtained in the form of a somewhat greasy mass. Yield 11.7 g. (74% of theory).

Workup

  1. customthe reaction mixture is evaporated
  2. additionDiethyl ether are added to the residue
  3. stirringas well as ice-cold 1N aqueous sodium hydroxide solution, shaken up
  4. customthe ethereal phase is separated off
  5. dry with materialAfter drying over anhydrous sodium sulphate
  6. customthe sulphate is precipitated from it by the dropwise addition of concentrated sulphuric acid, which
  7. filtrationis filtered off with suction
  8. washwashed with diethyl ether
  9. customis obtained in the form of a somewhat greasy mass

Sources & evidence

ORD record
ord-9140d3df86234b33aca57c2d225d3933
Source dataset
uspto-grants-1991_08
Patent number
US05037990

Reaction notes

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