Tetrahydrofuran → Benzoic acid, 4-hexyl-, methyl ester

HRID 1795375

Reaction equation

HRID 1795375 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[CH:6][CH:5]=1.C1COCC1.[CH2:17]([Mg]Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CN1CCCC1=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14307Methyl 4-chlorobenzoateHCID 178444609HCID 178444609, compound

Product 1

HCID 591633Benzoic acid, 4-hexyl-, methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A flame-dried two-necked flask is charged under argon with 4-chlorobenzoic acid methyl ester (0.5 g, 2.93 mmol), FeCl2 (19 mg, 0.15 mmol), THF (7 mL) and N-methylpyrrolidone (NMP, 1 mL). A solution of n-hexylmagnesium bromide (2M in Et2O, 1.9 mL, 3.8 mmol) is added via syringe to the resulting red solution, causing an immediate color change to dark brown and finally to violet. The resulting mixture is stirred for 5 min. Work-up as described above provides 4-hexylbenzoic acid methyl ester as a colorless syrup (90%). The spectroscopic and analytical data are identical to those compiled above.

Sources & evidence

ORD record
ord-c06d75318af34b4e8de8eb8da5585337
Source dataset
uspto-grants-2006_04
Patent number
US07026478B2

Linked notes

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