Triphenylphosphine → Phosphonium, [2-(1,3-dioxolan-2-yl)ethyl]triphenyl-, bromide (1:1)

HRID 1758161Notes

Reaction equation

HRID 1758161 reaction equation
[Br:1][CH2:2][CH2:3][CH:4]1[O:8][CH2:7][CH2:6][O:5]1.[C:9]1([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[Br-:1].[O:5]1[CH2:6][CH2:7][O:8][CH:4]1[CH2:3][CH2:2][P+:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 877762-(2-Bromoethyl)-1,3-dioxolane

Product 1

HCID 2733834Phosphonium, [2-(1,3-dioxolan-2-yl)ethyl]triphenyl-, bromide (1:1)Yield 27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 25 g. (0.138 mmole) of 2-(2-bromoethyl)-1,3-dioxolane and 36.2 g. (0.138 mmole) of triphenylphosphine in 30 ml. of toluene was heated at 100° C. for 18 hours. The reaction was cooled to yield two phases. The toluene phase was decanted and the oil remaining crystallized at -78° C. in ethyl acetate. Decantation of the ethyl acetate and warming of the crystals to room temperature gave an oil. The oil was dried under vacuum (0.05 torr) at 100° C. for 16 hours to yield 15 g. (27%) of the title compound as a solid glass which was ground to a powder.

Workup

  1. temperatureThe reaction was cooled
  2. customto yield two phases
  3. customThe toluene phase was decanted
  4. customthe oil remaining crystallized at -78° C. in ethyl acetate
  5. customgave an oil
  6. customThe oil was dried under vacuum (0.05 torr) at 100° C. for 16 hours
  7. customto yield 15 g

Sources & evidence

ORD record
ord-c8c15702624f4bbab2ba8625deb02aba
Source dataset
uspto-grants-1983_02
Patent number
US04371720

Reaction notes

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