1-Bromohexane → 2,4-Bis(5-hexyl-4-hexyloxy-2-hydroxyphenyl)-6-phenyl-s-triazine

HRID 743860Notes

Reaction equation

HRID 743860 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][C:3]=1[C:15]1[N:20]=[C:19]([C:21]2[CH:26]=[C:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:24]([OH:33])=[CH:23][C:22]=2[OH:34])[N:18]=[C:17]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:16]=1.[OH-].[K+].Br[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]>C(OCCO)C>[CH2:27]([C:25]1[C:24]([O:33][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:23][C:22]([OH:34])=[C:21]([C:19]2[N:20]=[C:15]([C:3]3[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:6]([O:8][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])=[CH:7][C:2]=3[OH:1])[N:16]=[C:17]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[N:18]=2)[CH:26]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 14797Potassium HydroxideHCID 1358435902,4-Bis(2,4-dihydroxy-5-hexylphenyl)-6-phenyl-s-triazine

Product 1

HCID 1358435992,4-Bis(5-hexyl-4-hexyloxy-2-hydroxyphenyl)-6-phenyl-s-triazine

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
90 °C

Procedure

To a 350 mL sulfonation flask equipped with a mechanical stirrer, condenser, dropping funnel and a nitrogen atmosphere are charged 16.2 g (30 mmol) of the product of Example 62, 3.7 g (66 mmol) of powdered potassium hydroxide and 100 mL of 2-ethoxyethanol. To the resulting red solution are then added 10.9 g (66 mmol) of 1-bromohexane are added dropwise over 30 minutes. The mixture is heated to 90° C. for 20 hours and filtered hot. The filtrate is warmed to 100° C. and 1 mL of acetic acid is added. The solution is cooled to 0° C. to give a precipitate. The crude yellow product is recrystallized from 70 mL of 2-ethoxyethanol to give the title compound in a yield of 13.1 g as a yellow solid melting at 118°-121° C.

Workup

  1. customTo a 350 mL sulfonation flask equipped with a mechanical stirrer, condenser
  2. additionare added dropwise over 30 minutes
  3. filtrationfiltered hot
  4. temperatureThe filtrate is warmed to 100° C.
  5. addition1 mL of acetic acid is added
  6. temperatureThe solution is cooled to 0° C.
  7. customto give a precipitate
  8. customThe crude yellow product is recrystallized from 70 mL of 2-ethoxyethanol

Sources & evidence

ORD record
ord-3b7d096ad72f465bad58bcb109d57d6f
Source dataset
uspto-grants-1996_09
Patent number
US05556973

Reaction notes

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