Lithium hydroxide, monohydrate → 3-(4-Chlorophenyl)-2-phenylpropanoic acid

HRID 488581Notes

Reaction equation

HRID 488581 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.O.[OH-].[Li+]>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 16098314Methyl 3-(4-chlorophenyl)-2-phenylpropionate

Product 1

HCID 222705593-(4-Chlorophenyl)-2-phenylpropanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of methyl 3-(4-chlorophenyl)-2-phenylpropionate (Step A, 20 g, 74 mmol) in acetonitrile (100 mL) and water (100 mL) was added lithium hydroxide monohydrate (8.8 g, 0.21 mol). After stirring at room temperature for 3 days, the volatile materials were removed by concentrating on a rotary evaporator and the residue was partitioned between water (300 mL) and hexane/ether (1:1, 200 mL). The water layer was separated, acidified to pH=2-3, and extracted with EtOAc (2×200 mL) The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.34-7.10 (m, 9H), 3.82 (dd, 1H), 3.36 (dd, 1H), 2.98 (dd, 1H).

Workup

  1. customthe volatile materials were removed
  2. concentrationby concentrating on a rotary evaporator
  3. customthe residue was partitioned between water (300 mL) and hexane/ether (1:1, 200 mL)
  4. customThe water layer was separated
  5. extractionextracted with EtOAc (2×200 mL) The combined organic extracts
  6. dry with materialwere dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-63a0c8393aad411ba93c05879d406315
Source dataset
uspto-grants-2005_12
Patent number
US06972295B2

Reaction notes

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