Sodium Hydroxide → HCID 14990622, compound

HRID 2166044Notes

Reaction equation

HRID 2166044 reaction equation
[OH-].[Na+].[OH:3][N:4]1[C:8]2[CH:9]=[C:10]([CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[OH:14])[CH:11]=[CH:12][C:7]=2[N:6]=[N:5]1>CO>[CH2:12]([O:3][N:4]1[C:8]2[CH:9]=[C:10]([CH:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[OH:14])[CH:11]=[CH:12][C:7]=2[N:6]=[N:5]1)[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 149906211-hydroxy-alpha-phenyl-1H-benzotriazole-6-methanol

Product 1

HCID 14990622HCID 14990622, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 1.2 parts of sodium hydroxide in 40 parts of methanol were added 7.8 parts of 1-hydroxy-α-phenyl-1H-benzotriazole-6-methanol. After concentration, 18 parts of methylbenzene were added to the concentrate. The solvent was evaporated again and the residue was dissolved in 27 parts of N,N-dimethylformamide. 5.52 Parts of 1-iodobutane were added at once and the whole was stirred for 30 minutes at 50° C. After concentration, 30 parts of water were added. The solidified product was filtered off, washed with water and dissolved in dichloromethane. The organic layer was dried, filtered and evaporated. The residue was crystallized from 17.5 parts of 2,2'-oxybispropane. The product was filtered off and dried, yielding 7.8 parts (87.4%) of 1-butoxy-α-phenyl-1H-benzotriazole-6-methanol; mp. 89.2° C. (int. 65).

Workup

  1. concentrationAfter concentration, 18 parts of methylbenzene
  2. additionwere added to the concentrate
  3. customThe solvent was evaporated again
  4. dissolutionthe residue was dissolved in 27 parts of N,N-dimethylformamide
  5. addition5.52 Parts of 1-iodobutane were added at once and the whole
  6. concentrationAfter concentration, 30 parts of water
  7. additionwere added
  8. filtrationThe solidified product was filtered off
  9. washwashed with water
  10. dissolutiondissolved in dichloromethane
  11. customThe organic layer was dried
  12. filtrationfiltered
  13. customevaporated
  14. customThe residue was crystallized from 17.5 parts of 2,2'-oxybispropane
  15. filtrationThe product was filtered off
  16. customdried

Sources & evidence

ORD record
ord-810233fd342b49249f5b38205c0f1d41
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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