Benzenepropanoic acid → Butyl 3-phenylpropanoate

HRID 1448437Notes

Reaction equation

HRID 1448437 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.[CH2:12](O)[CH2:13][CH2:14][CH3:15].C1CCC(N=C=NC2CCCCC2)CC1.C(O)(=O)C>N1C=CC=CC=1>[C:1]1([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 107Benzenepropanoic acidHCID 176Acetic AcidHCID 2631-ButanolHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 568855Butyl 3-phenylpropanoateYield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 3-phenylpropionic acid (15.0 g) and 1-butanol (8.15 g) in pyridine (30 ml) pTSA (0.100 g) is added. When the solution is homogeneous, DCC (24.8 g) is added, and the solution is stirred at room temperature for 24 h. After addition of acetic acid (10 ml) the reaction mixture is worked up as in Example 1. A 96% yield of butyl 3-phenylpropionate is obtained, b. p. 112°-3° C. (1 mm Hg) [lit. (12), 91° C. (0.3 mm Hg)].

Workup

  1. additionis added

Sources & evidence

ORD record
ord-b37f0f15989f4ebea515d2ff4abb04d4
Source dataset
uspto-grants-1979_12
Patent number
US04180504

Reaction notes

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