Sodium Hydroxide → 2-(1,1'-Biphenyl)-4-YL-2-hydroxypropanoic acid

HRID 369156Notes

Reaction equation

HRID 369156 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:14])([CH3:13])[C:8]([O:10]CC)=[O:9])=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:14])([CH3:13])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21184093Ethyl 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate

Product 1

HCID 33670892-(1,1'-Biphenyl)-4-YL-2-hydroxypropanoic acidYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude ethyl 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate was saponified by treating with 100 mL of ethanol and 100 mL of 4.0M NaOH solution. The suspension was stirred for 3 hours, after which a clear solution formed The solution was concentrated, diluted with 150 mL of H2O, washed with 2×50 mL of ether, and acidified to pH 1 with 10% HCl solution. The aqueous phase was extracted with 3×100 mL portions of ether and the combined ether extracts were washed with 50 mL of H2O, 50 mL of brine, dried (MgSO4) and concentrated leaving 18.3 g (72% yield) of racemic 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionic acid as a white solid after was recrystallization from CHCl3 and hexanes.

Workup

  1. customafter which a clear solution formed The solution
  2. concentrationwas concentrated
  3. additiondiluted with 150 mL of H2O
  4. washwashed with 2×50 mL of ether
  5. extractionThe aqueous phase was extracted with 3×100 mL portions of ether
  6. washthe combined ether extracts were washed with 50 mL of H2O, 50 mL of brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cfd6b6d4522e4ee1885c05287dfc4f6e
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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