Sodium Hydroxide → HCID 15233472, compound

HRID 1492832Notes

Reaction equation

HRID 1492832 reaction equation
C[O:2][C:3](=[O:44])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH:7]=[C:6]([O:27][CH2:28][CH2:29][CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:34][CH:33]=2)[CH:5]=1.[OH-].[Na+]>CO.O1CCOCC1>[C:18]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][CH2:11][O:10][C:8]2[CH:9]=[C:4]([CH:5]=[C:6]([O:27][CH2:28][CH2:29][CH2:30][O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)=[CH:34][CH:33]=3)[CH:7]=2)[C:3]([OH:44])=[O:2])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15233464HCID 15233464, compound

Product 1

HCID 15233472HCID 15233472, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.5 g (2.55 mmol) of 3,5-bis[3-(1,1'-biphenyl-4-yloxy)propoxy]benzoic acid methyl ester and 15 mL (15 mmol) of 1N NaOH in 45 mL of methanol and 40 mL of dioxane was stirred at reflux for 6 hours. The reaction mixture was concentrated at reduced pressure, the residue was acidified and the product was filtered and recrystallized from ethyl acetate to give 1.3 g (89% yield, mp 186°-187°) of 3,5-bis[3-(1,1'-biphenyl-4-yloxy)propoxy]benzoic acid.

Workup

  1. temperatureat reflux for 6 hours
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. filtrationthe product was filtered
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-953037a90d4d45a998fe93fcab9c8054
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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