Hydroquinone → HCID 86734548, Verbindung

HRID 596887

Reaktionsgleichung

Reaktionsgleichung von HRID 596887
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][OH:10])[CH:4]=1.[C:11]([C:13](=[CH2:17])[C:14]([O-:16])=[O:15])#[N:12].C1(=O)OC(=O)C=C1.C1(C=CC(O)=CC=1)O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C(C)=CC=CC=1>[C:11]([C:13](=[CH2:17])[C:14]([OH:16])=[O:15])#[N:12].[C:11]([C:13](=[CH2:17])[C:14]([OH:16])=[O:15])#[N:12].[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][OH:10])[CH:4]=1

Komponenten

7

Edukt 5

HCID 785HydroquinoneHCID 7923Maleic Anhydride2×HCID 14812Phosphorus oxide (P4O10)HCID 693741,3-BenzenedimethanolHCID 21226398HCID 21226398, Verbindung

Produkt 1

HCID 86734548HCID 86734548, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture consisting of 30.0 g (0.0474 mole) bisanthracene adduct/1,3-bis (hydroxymethyl) benzene bits (2-cyanoacrylate), 27.8 g (0.284 mole) maleic anhydride, 0.1 g hydroquinone, and 0.5 g phosphorous pentoxide in 125 ml. dry xylene is heated at 139°-141° C for 5 hours, cooled to room temperature, and suction-filled to give 26.1 g, mp 257°-259° C, of A/MA adduct. Solvent stripping of the filtrate and crystallization of the residue from benzene gives another 3.5 g, mp 258°-260° C, of A/MA adduct. The mother liquor is solvent stripped and the excess maleic anhydride sublimed off at 60°-65° C/0.1-0.2mm. The semi-crystalline residue (11.4g) is taken-up in 50 ml. hot benzene, the solution decanted from some insolubles (3.5 g, mp>300° C) and cooled to give another 1.3 g, mp 260°-262° C, of A/MA adduct. The filtrate is concentrated in vacuo to give 6.2 g (44% theory) of crude monomer as a pale orange liquid. IR and NMR analysis indicated the presence of considerable anhydride-containing and other unknown impurities.

Aufarbeitung

  1. additionsuction-filled
  2. customto give 26.1 g, mp 257°-259° C
  3. customSolvent stripping of the filtrate and crystallization of the residue from benzene
  4. customgives another 3.5 g, mp 258°-260° C
  5. customsublimed off at 60°-65° C
  6. customhot benzene, the solution decanted from some insolubles (3.5 g, mp>300° C)
  7. temperaturecooled
  8. customto give another 1.3 g, mp 260°-262° C
  9. concentrationThe filtrate is concentrated in vacuo
  10. customto give 6.2 g (44% theory) of crude monomer as a pale orange liquid
  11. additioncontaining

Quellen und Nachweise

ORD-Eintrag
ord-b1bcacf03dce421c9efb06cf7c96c427
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04012402

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