Reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[CH3:15]I.O=O.[OH-].[Na+]>O.C(O)C>[CH3:15][S:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Into a 3-neck round-bottom flask fitted with a condenser and an addition funnel were added 20 g of 11-mercaptoundecanoic acid, 13 g of methyl iodide and 200 mL of ethanol. A slow flow of nitrogen through the reactor was started to exclude oxygen because mercaptans can be converted into disulfides in the presence of air and strong alkali. A solution of 7.33 g of sodium hydroxide in 14.66 g of water was added dropwise to the reaction mixture via the addition funnel. Any unreacted methyl iodide, the ethanol and the water were removed using a rotovap. The residue was acidified using a mixture of concentrated hydrochloric acid and ice. After isolation the product was distilled. After a small amount of a low boiling fraction was collected, the crude product was collected at ~1 nun of Hg at 180° C. weighing 22.75 g. The crude product was distilled to yield 12.5 g of desired product representing 58.7% of theoretical based upon the weight of starting 11-mercaptoundecanoic acid.
Workup
- customInto a 3-neck round-bottom flask fitted with a condenser and an addition funnel
- customAny unreacted methyl iodide, the ethanol and the water were removed
- additiona mixture of concentrated hydrochloric acid and ice
- distillationAfter isolation the product was distilled
- customAfter a small amount of a low boiling fraction was collected
- customthe crude product was collected at ~1 nun of Hg at 180° C.
- distillationThe crude product was distilled
Sources & evidence
- ORD record
- ord-c8a5a0360b7f49ff962833e09726e49f
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05364959
Linked notes
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