Toluene → Isononanol

HRID 2215876

Reaction equation

HRID 2215876 reaction equation
C1(C)C=CC=CC=1.[Na].[CH3:9][CH:10]([CH3:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O-])=[O:17]>CO>[CH3:9][CH:10]([CH3:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17]

Participants

5

Reactant 3

HCID 1140TolueneHCID 5360545SodiumHCID 219533777-Methyloctanoate

Product 1

HCID 17072IsononanolYield 105.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar reaction as in 1 above, 100 ml toluene, sodium (39.5 g, 1.72 mole), 7-methyl-octanoate (52 g, 0.29 mole), and 260 ml anhydrous methanol reacted to yield 7-methyl-1-octanol (44.3 g, yield rate 85%); 7-methyl-1-octanol (44.3 g, 0.31 mole) reacted with chloro-chromic pyridine (100 g, 0.465 mole) to yield 7-methyl-octanaldehyde (31 g, yield rate 70%); and finally, 7-methyl-octanaldehyde (20 g, 0.14 mole), malonic acid (15 g, 0.14 mole), and 15 ml pyridine were added together and refluxed with heating for 3 hours. After cooling down 15 ml 30% sulfuric acid was added and the reaction mixture was stirred for 3 hours under ice bath and then extracted by diethyl ether. Diethyl ether was removed by evaporation and product was subject to vacuum fractional distillation and 122° C./1.5 mmHg fraction was collected as 9-methyl-2-decenoic acid (16 g, yield rate 80%).

Workup

  1. customIn a similar reaction as in 1 above

Sources & evidence

ORD record
ord-bcb746465a6340fdb861ebd1fc09d9cd
Source dataset
uspto-grants-2006_09
Patent number
US07109364B2

Linked notes

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