Sodium Iodide → Iodomethyl hexanoate

HRID 36324

Reaction equation

HRID 36324 reaction equation
[C:1]([O:8][CH2:9]Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[I-].[Na+].C(OC[I:21])(=O)C(C)(C)C>CC(C)=O>[C:1]([O:8][CH2:9][I:21])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 104401Iodomethyl pivalateHCID 525229Chloromethyl hexanoate

Product 1

HCID 12775069Iodomethyl hexanoateYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Chloromethyl hexanoate (205 mg, 1.25 mmol) was stirred with sodium iodide (900 mg, 6.0 mmol) in 3 mL of dry acetone for 4 hours at room temperature. Work-up followed the procedure detailed in EXAMPLE 3 above for the preparation of iodomethyl pivalate. Iodomethyl hexanoate, CH3 (CH2)4COOCH2I, was obtained as a yellow oil in 78% yield. NMR values were consistent with the assigned structure.

Sources & evidence

ORD record
ord-f26bb85210104c488af55ec157d8b6d1
Source dataset
uspto-grants-1995_05
Patent number
US05413996

Linked notes

Loading…