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

HRID 1648979Notes

Reaction equation

HRID 1648979 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aa17c3b452174eee94c2dff4cdb48bc3
Source dataset
uspto-grants-1983_11
Patent number
US04414393

Reaction notes

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