Glycidyl n-octyl ether → 2-[2-Hydroxy-4-(3-n-octyloxy-2-hydroxypropoxy)phenyl]-2H-benzotriazole

HRID 2164381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2164381
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]2=[N:10]1.[CH2:18]([O:26][CH2:27][CH:28]1[O:30][CH2:29]1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.CN1CCCC1=O>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:29][CH:28]([OH:30])[CH2:27][O:26][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:5]=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]2=[N:10]1

Komponenten

5

Edukt 2

HCID 92955Glycidyl n-octyl etherHCID 110641672-(2,4-dihydroxyphenyl)-2H-benzotriazole

Produkt 1

HCID 202305442-[2-Hydroxy-4-(3-n-octyloxy-2-hydroxypropoxy)phenyl]-2H-benzotriazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)KatalysatorHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A mixture of 2-(2,4-dihydroxyphenyl)-2H-benzotriazole (7.0 grams, 0.031 mole), 3-n-octyloxy-1,2-epoxypropane (10.7 grams, 0.046 moles), N-methyl-2-pyrrolidone (40 ml) and ethyltriphenylphosphonium bromide (0.2 gram) was heated for four hours at 135°-150° C. The solvent and excess epoxide were then removed by distillation. The resulting residue was dissolved in methylene chloride, washed with hydrochloric acid, water and sodium chloride solution before passing through a silica gel column. The product was obtained as a yellow oil which crystallized on standing. Recrystallization from heptane gave the above named product with a melting point of 51°-55° C.

Aufarbeitung

  1. temperaturewas heated for four hours at 135°-150° C
  2. customThe solvent and excess epoxide were then removed by distillation
  3. dissolutionThe resulting residue was dissolved in methylene chloride
  4. washwashed with hydrochloric acid, water and sodium chloride solution
  5. customThe product was obtained as a yellow oil which
  6. customcrystallized
  7. customRecrystallization from heptane
  8. customgave the

Quellen und Nachweise

ORD-Eintrag
ord-ba315c2154864bd69bf901283fc0190f
Quelldatensatz
uspto-grants-1985_03
Patentnummer
US04504419

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