Ethylene Glycol → 71935-16-5

HRID 263329Notes

Reaction equation

HRID 263329 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 6 N 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-14e02f5aeb0948b681d2c164e5773c05
Source dataset
uspto-grants-1979_05
Patent number
US04156734

Reaction notes

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