Sodium hydride → Ethyl 6,12-dithiatetradecanoate

HRID 1898770Notes

Reaction equation

[CH2:1]([S:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][SH:9])[CH3:2].[H-].[Na+].I[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>>[C:17]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][S:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][S:3][CH2:1][CH3:2]

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 4169827Ethyl 5-iodopentanoate

HCID 234238685-Ethylthiopentanethiol

Product 1

HCID 15020143Ethyl 6,12-dithiatetradecanoate

Procedure

To illustrate the preparation of the dithia-substituted fatty acid ethers, 5-ethylthiopentane thiol can be reacted with sodium hydride and the resulting product reacted with ethyl 5-iodovalerate to yield ethyl 6,12-dithiatetradecanoate. The ester group can then be removed by treatment with alkali metal hydroxide, e.g. NaOH, to produce the desired 6,12-dithiatetradecanoic acid.

Sources & evidence

ORD record: ord-69511f4b542842f19c9e40de0bce29bb
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571689

Reaction notes

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