Hydrochloric Acid → HCID 178443314, compound
Reaction equation
[SH:1]CCC(O)=O.[CH3:7][O-:8].[Na+].[Na].C1(C)C=CC(S(O[CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH3:29])(=O)=O)=CC=1.Cl.C(O[CH2:35][CH3:36])C>CO>[CH2:27]([CH2:28][CH2:29][C:7]([OH:8])=[S:1])[CH2:26]/[CH:25]=[CH:24]/[CH2:23]/[CH:22]=[CH:21]/[CH2:35][CH3:36]Participants
Conditions
- Temperature
- 40 °C
Procedure
3-Mercaptopropionic acid (150 mg, 1.41 mmol, 1.5 eq) can be added, under an atmosphere of dry nitrogen, to a stirred solution of sodium methoxide, prepared from sodium (64 mg, 2.78 mmol, 3 eq) and methanol (20 ml). After the initial white precipitate had dissolved, a solution of (3Z,6Z)-nona-3,6-dienyl p-toluenesulfonate (276 mg, 0.94 mmol) in diethyl ether can be added. The mixture can be stirred at 40° C. for several days under nitrogen, hydrochloric acid (10% v/v, 20 ml) and diethyl ether (20 ml) can be poured into the crude reaction mixture. The organic phase can be collected and washed with water and brine, and dried over sodium sulfate. The 3-(3E,6E)-nona-3,6-dienylthiopropionic acid produced can be dissolved in a solvent and PhSeBr and HgCl2 can added to the solution followed by an oxidizing agent to form a nitro-vinyl group at either on the 3-(3E,6E)-nona-3,6-dienylthiopropionic acid thereby producing, 3-(3E,6E)-6-nitronona-3,6-dienylthiopropionic acid.
Workup
- dissolutionAfter the initial white precipitate had dissolved
- customreaction mixture
- customThe organic phase can be collected
- washwashed with water and brine
- dry with materialdried over sodium sulfate
Sources & evidence
- ORD record
- ord-84caac542236469a837f392237cd10fd
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08686167B2
Reaction notes
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