Hydrochloric Acid → HCID 54100633, compound

HRID 980323Notes

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 soution is obtained. This is cooled to -10° C. and 15-chloro-3-methylene-7,11,15-trimethyl-hexadeca-1,6,10-triene (10 g) are then added followed, over the course of 1 hour, by dry hydrogen chloride gas (3.9 g). The reaction mixture is poured into an aqueous solution (100 cc) of ammonium chloride (100 g/liter). The organic phase is separated off by decanting and the aqueous phase is 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 separated off
customby decanting
extractionthe aqueous phase is 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-882a0f3bd12148dd831ee947a1943ee5
Source dataset: uspto-grants-1987_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04636570

Reaction notes

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