Potassium Hydroxide → 2-(2-Phenylethyl)malonic acid

HRID 1003972

Reaction equation

HRID 1003972 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]([C:15]([O:17]CC)=[O:16])[C:10]([O:12]CC)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>O>[C:1]1([CH2:7][CH2:8][CH:9]([C:15]([OH:17])=[O:16])[C:10]([OH:12])=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 811191,3-Diethyl 2-(2-phenylethyl)propanedioate

Product 1

HCID 1012342-(2-Phenylethyl)malonic acidYield 65.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of diethyl 2-phenylethylmalonate (3.61 g) and potassium hydroxide (1.69 g, 2.5 eq) in water (15 ml) was refluxed for 2 h and cooled to room temperature. The solution was washed with diethyl ether (2×10 ml) and then acidified to pH 2 (5M hydrochloric acid). The aqueous phase was extracted with diethyl ether (2×20 ml). The combined extracts were washed with water (2×20 ml), saturated brine (20 ml), dried (MgSO4) and evaporated to give the title compound as a white solid (1.85 g, 65%); νmax (KBr) 3080(br), 1705 cm-1 ; δH [(CD3)2CO], 2.18 (2H, m, CH2), 2.70 (2H, m, CH2), 3.40 (1H, t, J 7.4 Hz, CH), 7.25 (5H, m, Ph). DCIMS MNH4+ 226.

Workup

  1. temperaturewas refluxed for 2 h
  2. washThe solution was washed with diethyl ether (2×10 ml)
  3. extractionThe aqueous phase was extracted with diethyl ether (2×20 ml)
  4. washThe combined extracts were washed with water (2×20 ml), saturated brine (20 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-0c7bebdcc3944904a183e41c6cfc24be
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Linked notes

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