Hydrochloric Acid → HCID 54100633, compound

HRID 978911Notes

Reaction equation

[ClH:1].C(N(CC)CC)C.[Cl:9][C:10]([CH3:29])([CH3:28])[CH2:11][CH2:12][CH2:13][C:14]([CH3:27])=[CH:15][CH2:16][CH2:17][C:18]([CH3:26])=[CH:19][CH2:20][CH2:21][C:22](=[CH2:25])[CH:23]=[CH2:24].[ClH:30].[Cl-:31].[NH4+]>C(O)(=O)C.C(Cl)Cl>[Cl:1][CH2:24][CH:23]=[C:22]([CH3:25])[CH2:21][CH2:20][CH2:19][C:18]([Cl:31])([CH3:26])[CH2:17][CH2:16][CH2:15][C:14]([Cl:30])([CH3:27])[CH2:13][CH2:12][CH2:11][C:10]([Cl:9])([CH3:29])[CH3:28]

Participants

Conditions

Temperature: -10 °C

Procedure

Triethylamine hydrochloride (0.48 g), methylene chloride (15 cc), acetic acid (10 cc) and cuprous chloride (90 mg) are introduced, under an argon atmosphere, into a 250 cc reactor. The reaction mixture is stirred until a homogeneous solution is obtained. This is cooled to -10° C. and 15-chloro-3-methylene-7,11,15-trimethyl-hexadeca-1,6,10-triene (10 g) is then added followed, over the course of 1 hour, by dry gaseous hydrogen chloride (3.9 g). The reaction mixture is poured into an aqueous solution (100 cc) of ammonium chloride (100 g/liter). The organic phase is removed by decanting and the aqueous phase is then extracted with methylene chloride (twice 100 cc). The combined organic phases are washed with water (100 cc) and then dried over potassium carbonate. After filtration and evaporation of the solvent, 1,7,11,15-tetrachloro-3,7,11,15-tetramethyl-hexadec-2-ene (13.1 g) is obtained in a yield of 96.5%.

Workup

customis obtained
customThe organic phase is removed
customby decanting
extractionthe aqueous phase is then extracted with methylene chloride (twice 100 cc)
washThe combined organic phases are washed with water (100 cc)
dry with materialdried over potassium carbonate
filtrationAfter filtration and evaporation of the solvent

Sources & evidence

ORD record: ord-46518c3778784b6bb7170c4be0757af1
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04665244

Reaction notes

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