Potassium Hydroxide → Propanedioic acid, 2-(3-phenylpropyl)-

HRID 1003975Notes

Reaction equation

HRID 1003975 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([C:16]([O:18]CC)=[O:17])[C:11]([O:13]CC)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>C(O)C.O>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([C:16]([OH:18])=[O:17])[C:11]([OH:13])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 106363121,3-Diethyl 2-(3-phenylpropyl)propanedioate

Product 1

HCID 95205Propanedioic acid, 2-(3-phenylpropyl)-Yield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of diethyl 3-phenylpropylmalonate (5.5 g) and potassium hydroxide (2.8 g, 2.5 eq) in ethanol (20 ml) and water (30 ml) was refluxed for 5 hours. Work-up as described in Example 37b) gave the title compound (4.3 g, 98%); νmax (CH2Cl2) 2940 (br), 1727 and 1413cm-1 ; δH (CDCl3) 1.73 (2H, m, CH2), 2.00 (2H, m, CH2), 2.66 (2H, t, J 7.5 Hz, CH2), 3.44 (1H, t, J 6.8 Hz, CH), 6.84 (2H, bs, 2×CO2H), 7.26 (5H, m, Ph). EIMS M+ 222, DCIMS MNH4+ 240.

Workup

  1. temperaturewas refluxed for 5 hours

Sources & evidence

ORD record
ord-6bd5aad7a1bc40a3889c0488270df7df
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Reaction notes

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