Benzenepropanoic acid → isopropyl 3-phenylpropionate

HRID 1448440Notes

Reaction equation

HRID 1448440 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:12](O)([CH3:14])[CH3:13].C1CCC(N=C=NC2CCCCC2)CC1.C(O)(=O)C>N1C=CC=CC=1>[C:1]1([CH2:7][CH2:8][C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 107Benzenepropanoic acidHCID 176Acetic AcidHCID 3776IsopropanolHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 347496isopropyl 3-phenylpropionateYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 3-phenylpropionic acid (15.0 g) and isopropanol (6.61 g) in pyridine (30 ml) perchloric acid (0.150 g) and DCC (24.8 g) are added. After stirring at room temperature for 24 h acetic acid (10 ml) is added, and the reaction mixture is worked-up as described in Example 1 to give a 94% yield of isopropyl 3-phenylpropionate (b. p., see Example 2).

Workup

  1. additionare added
  2. additionis added

Sources & evidence

ORD record
ord-921dd62e7b874d999f7b6cdfec821df2
Source dataset
uspto-grants-1979_12
Patent number
US04180504

Reaction notes

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