Chloride → Stilbene

HRID 2255836Notes

Reaction equation

HRID 2255836 reaction equation
[Cl-].P1CCCCCCCC1.P(OC)(OC)OC.[C:18]1([CH:26]=[CH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:23]=[CH:22][C:21](C=O)=[CH:20][CH:19]=1>>[C:18]1([CH:26]=[CH:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 312ChlorideHCID 8472Trimethyl phosphiteHCID 141711HCID 141711, compoundHCID 23432754HCID 23432754, compound2×

Product 1

HCID 11502StilbeneYield 73%

Procedure

To improve the performance it was decided to synthesise distyrylbenzene (8). (Scheme 2) which should give emission at a longer wavelength, be a solid and have the required lack of symmetry and the necessary polymer compatibility. The first step in the synthesis of (8) was the reduction of (5) with lithium aluminium hydride under standard conditions to give the alcohol (9) in 82% yield. The alcohol (9), dissolved in 1,4-dioxane, was treated with concentrated hydrochloric acid to yield (10) in 89% yield. The chloride (10) was converted into the phosphonane (11) in 55% yield by treatment with trimethyl phosphite at reflux. The phosphonate (11) was coupled with 4-stilbenecarbaldehyde (12) under the same conditions used to form (4) and the distyrylbenzene (8) was isolated in 73% yield. ##STR6##

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-dd805caffd3e4da0a1225b0b67957dd9
Source dataset
uspto-grants-1997_08
Patent number
US05653914

Reaction notes

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