Sodium Hydroxide → 1,5-Bis(4'-carboxyphenyl)-3-pentanol

HRID 1089361Notes

Reaction equation

HRID 1089361 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]([OH:26])[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24]C)=[O:23])=[CH:18][CH:17]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>Cl>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][CH:13]([OH:26])[CH2:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=2)=[CH:21][CH:20]=1)([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14817494HCID 14817494, compound

Product 1

HCID 148174961,5-Bis(4'-carboxyphenyl)-3-pentanolYield 100%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 1,5-bis(4'-methoxycarbonylphenyl)-3-pentanol and 1 L of 3 M aqueous sodium hydroxide are heated at reflux for 7 hours, the resulting reaction mixture is allowed to cool to room temperature and added to a stirred mixture of 300 mL concentrated hydrochloric acid and 200 g of ice. The precipitate is collected by filtration and recrystallized from 3 L of acetic acid. The purified product is dried by heating under vacuum to give 330 g (100% of theory) of 1,5-bis(4'-carboxyphenyl)-3-pentanol as a white, fine, crystalline powder.

Workup

  1. temperatureare heated
  2. temperatureat reflux for 7 hours
  3. customthe resulting reaction mixture
  4. filtrationThe precipitate is collected by filtration
  5. customrecrystallized from 3 L of acetic acid
  6. customThe purified product is dried
  7. temperatureby heating under vacuum

Sources & evidence

ORD record
ord-25a7b1169604422f84b2250aa6ece9db
Source dataset
uspto-grants-1990_10
Patent number
US04965399

Reaction notes

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