Sodium Hydroxide → 5-(4-n-Nonylbenzoyl)pentanoic acid

HRID 1720145Notes

Reaction equation

HRID 1720145 reaction equation
[CH2:1]([C:10]1[CH:25]=[CH:24][C:13]([C:14]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]C)=[O:21])=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[OH-].[Na+]>C(O)C>[CH2:1]([C:10]1[CH:11]=[CH:12][C:13]([C:14]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:15])=[CH:24][CH:25]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22420381Methyl 5-(4-n-nonylbenzoyl)pentanoate

Product 1

HCID 152955655-(4-n-Nonylbenzoyl)pentanoic acidYield 71.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Adipic acid monomethyl ester (50 g; 0.31 mole) is converted to the acid chloride with thionyl chloride (50 g) in the manner described in Example 1. This product is reacted with nonylbenzene (400 ml) and aluminum chloride (80 g; 0.6 mole) and the product purified in a manner analogous to that described in Example 1 to provide methyl 5-(4-n-nonylbenzoyl)pentanoate (35.2 g). This ester (35 g) is hydrolysed with sodium hydroxide in aqueous ethanol as in Example 1 to give, on recrystallization from aqueous ethanol, 5-(4-n-nonylbenzoyl)pentanoic acid (24 g) as colorless crystals, m.p. 29°-31° C.

Sources & evidence

ORD record
ord-2804de78ab704d1aa5726a34591bb000
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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