Hydrochloric Acid → 4′-(2-Hydroxyethoxy)-2-methyl[1,1′-biphenyl]-4-carboxylic acid

HRID 2220640Notes

Reaction equation

HRID 2220640 reaction equation
O.[OH-].[Li+].[OH:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22]CC)=[O:21])=[CH:16][C:15]=2[CH3:25])=[CH:10][CH:9]=1.C(O)C.Cl>O.O1CCOCC1>[OH:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][C:15]=2[CH3:25])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 23134157HCID 23134157, compound

Product 1

HCID 231342804′-(2-Hydroxyethoxy)-2-methyl[1,1′-biphenyl]-4-carboxylic acidYield 53.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Lithium hydroxide monohydrate (0.19 g) was added to a mixture of ethyl 4′-(2-hydroxyethoxy)-2-methylbiphenyl-4-carboxylate (0.136 g), ethanol (2 mL), 1,4-dioxane (2 mL) and water (1 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 2 mol/L hydrochloric acid (2.3 mL). The solvent was evaporated under reduced pressure, and water and ethyl acetate were added to the residue. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethylacetate/n-hexane=2/1-4/1) to afford the title compound (0.066 g).

Workup

  1. customThe solvent was evaporated under reduced pressure, and water and ethyl acetate
  2. additionwere added to the residue
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: ethylacetate/n-hexane=2/1-4/1)

Sources & evidence

ORD record
ord-f530fb312bda47f5ba0ae0eccdcfff49
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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