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

HRID 463787Notes

Reaction equation

HRID 463787 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-fa9d34ed3b7046d989116aed3d36f44a
Source dataset
uspto-grants-1985_10
Patent number
US04544691

Reaction notes

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