Benzene → HCID 568965, compound

HRID 1579817Notes

Reaction equation

HRID 1579817 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>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

6

Reactant 4

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

Product 1

HCID 568965HCID 568965, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of sodium hydride (126 g. of a 57 percent 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 1.5 hours, poured into water and extracted with ether. The ether extracts are dried and concentrated to give an oil which is crystallized from ethanolwater 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 1.5 hours
  3. extractionextracted with ether
  4. dry with materialThe ether extracts are dried
  5. concentrationconcentrated
  6. customto give an oil which
  7. customis crystallized from ethanolwater
  8. customto give 220 g

Sources & evidence

ORD record
ord-2a5e544a9db346feb55e04598951d94b
Source dataset
uspto-grants-1976_01
Patent number
US03931328

Reaction notes

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