Water → 4-(6-Hydroxyhexyloxy)biphenyl-4'-carboxylic acid

HRID 890903Notes

Reaction equation

HRID 890903 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#N)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.[OH-:23].[K+].[OH2:25]>C(O)CO.CO>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:25])=[O:23])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 11173950HCID 11173950, compound

Product 1

HCID 222424974-(6-Hydroxyhexyloxy)biphenyl-4'-carboxylic acidYield 93.4%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 887MethanolSolvent

Procedure

To a solution of 8 (13.0 g, 4.4 mmol) in ethylene glycol (370 ml) was added KOH (37.07 g, 66.06 mmol). After refluxing for 2 h, the reaction mixture was poured into 1.6 L water for acidification to a pH less than 4. The precipitate from acidification was boiled in methanol to remove water and ethylene glycol. The solid residue collected by filtration was further purified by boiling in methylene chloride. The solid product was further washed with hot methylene chloride to yield 9 (12.94 g, 93.4%). 1H NMR spectral data (400 MHz, DMSO-d6): δ 1.30-1.50 (m, 6H, —CH2—), 1.74 (m, 2H, —CH2—), δ 3.40 (t, 2H, —CH2OAr), δ 4.01 (t, 2H, HOCH2—), δ 7.05 (d, 2H, aromatic rings), δ 7.67 (d, 2 H, aromatic rings), δ 7.74 (d, 2H, aromatic rings), δ 7.98 (d, 2H, aromatic rings).

Workup

  1. temperatureAfter refluxing for 2 h
  2. customto remove water and ethylene glycol
  3. filtrationThe solid residue collected by filtration
  4. customwas further purified
  5. washThe solid product was further washed with hot methylene chloride

Sources & evidence

ORD record
ord-6915d7baf49448efb027a7ea633ecabf
Source dataset
uspto-grants-2006_02
Patent number
US07001648B2

Reaction notes

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