Hydrochloric Acid → 2,4-Di-(2,4-dimethylphenyl)-6-[2-hydroxy-4-(6-hydroxy-1-hexyloxy)phenyl]-1,3,5-triazine

HRID 2210976Notes

Reaction equation

HRID 2210976 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[CH3:22])[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=2[OH:30])[N:10]=1.Cl[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38].[I-].[K+].[OH-].[Na+].Cl>C(C(C)=O)C(C)C.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[CH3:22])[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38])=[CH:25][C:24]=2[OH:30])[N:10]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 742762-(2,4-Dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazineHCID 748286-Chloro-1-hexanol

Product 1

HCID 1360840012,4-Di-(2,4-dimethylphenyl)-6-[2-hydroxy-4-(6-hydroxy-1-hexyloxy)phenyl]-1,3,5-triazineYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2,4-di-(2,4-dimethylphenyl)-6(2,4-dihydroxyphenyl)-1,3,5-triazine (20 g, 0.049 mole), 6-chloro-1-hexanol (7.04 g, 0.05 mole), available from Aldrich Chemicals, Milwaukee, Wis., potassium iodide (0.37 g, 0.0022 mole), PEG 400 (1.9 g, 0.005 mole), available from Aldrich Chemicals, Milwaukee, Wis., sodium hydroxide (2.0 g, 0.05 mole) in methyl isobutyl ketone was reflux (120°-122° C.) for 16 hrs. After cooling to 85° C., water (50 ml) was added and the reaction mixture was acidified with 37% hydrochloric acid to pH 1, and the resulting aqueous layer was removed. The organic layer was washed twice with warm water (75 ml per each washing) and the volatiles were removed under reduced pressure. The oily residue was dissolved in acetone and decolorized with activated charcoal and filtered. Cooling to 22° C. gave 2,4-di-(2,4-dimethylphenyl)-6-[2-hydroxy-4-(6-hydroxy-1-hexyloxy)phenyl]-1,3,5-triazine (I-E) as a pale yellow solid (10 g), m.p. 117°-118° C. The filtrate was concentrated under a reduced pressure to give a second crop of triazine I-E bringing the total weight of product to 21 g (87% yeild). It was characterized to be 2,4-di-(2,4,dimethylphenyl)-6-[ 2-hydroxy-4-(6-hydroxy-1-hexyloxy)phenyl]-1,3,5-triazine (I-E).

Workup

  1. customthe resulting aqueous layer was removed
  2. washThe organic layer was washed twice with warm water (75 ml per each washing) and the volatiles
  3. customwere removed under reduced pressure
  4. dissolutionThe oily residue was dissolved in acetone
  5. filtrationfiltered
  6. temperatureCooling to 22° C.

Sources & evidence

ORD record
ord-84983f6956c847f183b80841c06e5ab2
Source dataset
uspto-grants-1995_10
Patent number
US05461151

Reaction notes

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