Benzene → HCID 568965, compound

HRID 1576157Notes

Reaction equation

HRID 1576157 reaction equation
[H-].[Na+].C1C=CC=CC=1.[CH2:9]([OH:11])[CH3:10].[C:12]1([CH2:22][C:23]([OH:25])=O)[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]([OH:21])=O>C(O)C.O.O>[CH2:9]([O:11][C:19]([CH:18]1[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:22][C:23]1=[O:25])=[O:21])[CH3:10]

Participants

7

Reactant 4

HCID 241Benzene2×HCID 702EthanolHCID 24123o-Phenylenediacetic acidHCID 24758Sodium hydride

Product 1

HCID 568965HCID 568965, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

To a stirred mixture of sodium hydride (126 g. of a 57% suspension in nujol), 2000 ml. of benzene and 2 ml. of ethanol heated at its reflux temperature under dry nitrogen is added dropwise the diethyl ester of o-phenylene-diacetic acid (335.6 g.) in 700 ml. of benzene. The mixture is refluxed for 1.5 hours, poured into water and extracted with ether. The ether extracts are dried and concentrated to give an oil which is crystallizied from ethanol-water to give 220 g. of the title product with m.p. 58°-61°.

Workup

  1. temperaturereflux temperature under dry nitrogen
  2. temperatureThe mixture is refluxed for 1.5 hours
  3. extractionextracted with ether
  4. dry with materialThe ether extracts are dried
  5. concentrationconcentrated
  6. customto give an oil which
  7. customto give 220 g

Sources & evidence

ORD record
ord-ce3bf4c85d6649389c81c8dc454d9cf9
Source dataset
uspto-grants-1976_09
Patent number
US03979434

Reaction notes

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