Ethylene Glycol → 71935-16-5

HRID 462246Notes

Reaction equation

HRID 462246 reaction equation
[OH-:1].[Na+].[CH2:3]([OH:6])[CH2:4]O.C(C1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)=[CH:11][CH:10]=1)#N>O>[N:15]1([C:12]2[CH:13]=[CH:14][C:4]([C:3]([OH:6])=[O:1])=[CH:10][CH:11]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 10220051HCID 10220051, compound

Product 1

HCID 1302130371935-16-5Yield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 180 ml of 6N NaOH, 360 ml ethylene glycol and 39.3 g (180 mmole) of 1-p-cyanophenylindole [Misbahul Ain Khan and J. B. Polya, J. Chem. Soc., 85 (1970)] is refluxed for 3 hours at 150°. The basic solution is diluted with 450 ml of H2O and extracted with diethyl ether to remove neutrals. The aqueous solution is acidified with 200 ml of 6N HCl. The solid is filtered washed with hot water and dried in a vacuum oven at 50° to yield 45.8 g (95%) of p-(indol-1-yl)benzoic acid, m.p. 224°-226°.

Workup

  1. temperatureis refluxed for 3 hours at 150°
  2. extractionextracted with diethyl ether
  3. customto remove neutrals
  4. filtrationThe solid is filtered
  5. washwashed with hot water
  6. customdried in a vacuum oven at 50°

Sources & evidence

ORD record
ord-a636dee042244f47820db6001ade146e
Source dataset
uspto-grants-1977_12
Patent number
US04065572

Reaction notes

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