Toluene → HCID 54480429, compound

HRID 2371770Notes

Reaction equation

HRID 2371770 reaction equation
[CH2:1]([OH:8])[C:2]#[C:3][C:4]#[C:5][CH2:6][OH:7].C(N(CC)CC)C.[CH2:16]1[CH2:20][O:19][CH2:18][CH2:17]1.[C:21](Cl)(=[O:30])[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:32]1(C)[CH:37]=[CH:36]C=[CH:34][CH:33]=1>>[C:21]([O:7][CH2:6][C:5]#[C:4][C:3]#[C:2][CH2:1][O:8][C:18](=[O:19])[CH:17]=[CH:16][C:20]1[CH:36]=[CH:37][CH:32]=[CH:33][CH:34]=1)(=[O:30])[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 5

HCID 1140TolueneHCID 8028Tetrahydrofuran3×HCID 8471TriethylamineHCID 660233-Phenylprop-2-enoyl chlorideHCID 94973Diacetylene glycol

Product 1

HCID 54480429HCID 54480429, compound

Conditions

Temperature
55 °C

Procedure

2,4-Hexadiyn-1,6-diol (66.1 g, 0.6 mole), triethylamine (70 g) and (THF) (400 ml) were charged into a 1-liter flask which was equipped with a mechanical stirrer, thermometer, gas inlet, and a dry ice condenser. The solution was brought to 50° C. under a blanket of nitrogen. A solution of cinnamoyl chloride (110 g, 0.6 moles) and THF (200 ml) was added through a dropping funnel to the above solution which was vigorously stirred over a period of one hour at 45°. The resulting solution was held for 5 hours at this temperature and then heated to 55° C. and held at this temperature for an additional 20 hours to complete the reaction, after which the THF was stripped off and the remaining solid was redissolved in 500 ml of toluene. The toluene solution was washed three times with water, dried over magnesium sulfate and filtered. After the toluene was removed from the filtrate, 134 g. of the colorless, crystalline 2,4-hexadiyn-1,6-diyl dicinnamate product having a m.p. of 102°-104° was identified by NMR and IR analyses. One gram of the dicinnamate was spread on a filter paper and subjected to UV irradiation at 254 nm. After 30 seconds, no color change was observed; indicating that this product is unsuitable for photoimaging.

Workup

  1. customwas equipped with a mechanical stirrer
  2. customwas brought to 50° C. under a blanket of nitrogen
  3. waitThe resulting solution was held for 5 hours at this temperature
  4. waitheld at this temperature for an additional 20 hours
  5. customthe reaction
  6. washThe toluene solution was washed three times with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customAfter the toluene was removed from the filtrate, 134 g
  10. customsubjected to UV irradiation at 254 nm
  11. waitAfter 30 seconds

Sources & evidence

ORD record
ord-82a6c0eee763471c91457d0dafb6a916
Source dataset
uspto-grants-1992_03
Patent number
US05095134

Reaction notes

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