Hexane → Triphenylphosphine hydrochloride

HRID 1982283Notes

Reaction equation

HRID 1982283 reaction equation
[Cl:1]CC=C(C)CCC=C(C)CCCC(C)C.[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCCCCC>C1(C)C=CC=CC=1>[Cl-:1].[C:30]1([PH+:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 11776TriphenylphosphineHCID 542136361-Chloro-3,7,11-trimethyl-dodeca-2,6-diene

Product 1

HCID 9882740Triphenylphosphine hydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

An amount of 9.1 grams (37 mmol) of 1-chloro-3,7,11-trimethyl-dodeca-2,6-diene and 9.8 grams (37 mmol) of triphenyl phosphine were heated to boiling in 30 ml of toluene for a period of five hours. The resultant suspension was mixed with 200 ml of hexane and after precipitation of the white solid material, the liquid was decanted. This mixing with hexane was repeated five times and the remaining tacky solid substance was dried under reduced pressure. An amount of 18.2 grams (3,7,11)-trimethyl-dodeca-2,6,10-trien-1-yl)triphenylphosphonium chloride (E/Z isomer mixture) was obtained. The yield was 87 percent of theory.

Workup

  1. customafter precipitation of the white solid material
  2. customthe liquid was decanted
  3. customthe remaining tacky solid substance was dried under reduced pressure

Sources & evidence

ORD record
ord-fd051021c8be4c49a5f9f8cf90269908
Source dataset
uspto-grants-1986_06
Patent number
US04595783

Reaction notes

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