Triphenylphosphine → 1-(4,4-Dimethyl-6-chromanyl)ethyltriphenylphosphonium bromide

HRID 2118520Notes

Reaction equation

[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([Br:14])[CH3:13])[CH:10]=2)[O:5][CH2:4][CH2:3]1.[C:16]1([P:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C(C)=CC=CC=1>[Br-:14].[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([P+:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH3:13])[CH:10]=2)[O:5][CH2:4][CH2:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

4.6 g of 4,4-dimethyl-6-(1-bromoethyl)chromane were dissolved in 40 ml of xylene and the solution was treated with 5.3 g of triphenylphosphine. The mixture was heated to 100° C. overnight, cooled, the precipitated cyrstals were filtered off under suction and washed with hexane. For the further purification, the phosphonium salt was dissolved in methylene chloride and precipitated again by the addition of ethyl acetate. There were obtained 3.5 g of [1-(4,4-dimethyl-6-chromanyl)ethyl]triphenylphosphonium bromide in the form of colorless crystals of melting point 142°-148° C.

Workup

temperaturecooled
filtrationthe precipitated cyrstals were filtered off under suction
washwashed with hexane
customFor the further purification
dissolutionthe phosphonium salt was dissolved in methylene chloride
customprecipitated again by the addition of ethyl acetate

Sources & evidence

ORD record: ord-c711d6a060a14596942f268544fa3f12
Source dataset: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04678793

Reaction notes

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