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

HRID 2232464Notes

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 crystals 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 crystals 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-7c5d57cec5024a6891348706ee2eb1e7
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04788213

Reaction notes

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