Lithium hydroxide, monohydrate → 3,3-Bis(p-chlorophenyl)propionic acid

HRID 30364Notes

Reaction equation

HRID 30364 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:9][C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.O.[OH-].[Li+]>CO.C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22270432Methyl 3,3-Bis(4-chlorophenyl)propionate

Product 1

HCID 756813,3-Bis(p-chlorophenyl)propionic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of methyl 3,3-bis(4-chlorophenyl)propionate (Step B, 0.78 g, 3.9 mmol), lithium hydroxide monohydrate (0.33 g, 7.8 mmol) in 1:1:1 MeOH/THF/water (15 mL) was stirred at room temperature overnight. The resulting mixture was partitioned between 2 M aqueous hydrochloric acid (50 mL) and ether (50 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×50 mL). The combined extracts were dried over anhydrous MgSO4, filtered, and concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.29-7.23 (m, 4H), 4.49 (t, 1H), 3.02 (d, 2H).

Workup

  1. customThe resulting mixture was partitioned between 2 M aqueous hydrochloric acid (50 mL) and ether (50 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with EtOAc (2×50 mL)
  4. dry with materialThe combined extracts were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-91f70f9e7a1f4fc09ac3bdecf882fc91
Source dataset
uspto-grants-2008_09
Patent number
US07423067B2

Reaction notes

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