Lithium Hydroxide → 4'-(3-chloropropoxy)[1,1'-biphenyl]-4-carboxylic Acid

HRID 429236Notes

Reaction equation

HRID 429236 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([O:20]C)=[O:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[OH-].[Li+]>C1COCC1.O>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 18354767Methyl 4'-(3-chloropropoxy)[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 183547594'-(3-chloropropoxy)[1,1'-biphenyl]-4-carboxylic AcidYield 82.3%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

The product from Example 10B (3.4 g, 11.2 mmol) and lithium hydroxide (1.2 g, 28.6 mmol) in THF:water (3:1, 52 mL) were stirred vigorously at ambient temperature for 24 hours. The volume of the mixture was reduced under reduced pressure and then extracted with hexanes (2×25 mL). The remaining aqueous phase was acidified to pH 2 and then extracted with ethyl acetate (3×50 mL). The ethyl acetate extract was evaporated under reduced pressure to provide the title compound as a solid (2.68 g).

Workup

  1. extractionextracted with hexanes (2×25 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. extractionThe ethyl acetate extract
  4. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-69443ec7a13b446b8db7e469a187aa62
Source dataset
uspto-grants-2001_11
Patent number
US06316475B1

Reaction notes

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