Water → HCID 23680093, compound

HRID 1937115Notes

Reaction equation

HRID 1937115 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[C:16]1(C)C(C)=CC=CC=1.[OH-:24].[Na+:25].[OH2:26]>>[C:11]([C:7]1[CH:8]=[C:9]([CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])[C:16]([O-:26])=[O:24])([CH3:14])([CH3:13])[CH3:12].[Na+:25]

Participants

5

Reactant 4

HCID 962WaterHCID 7237O-Xylene2×HCID 14798Sodium HydroxideHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 23680093HCID 23680093, compound

Conditions

Temperature
160 °C

Procedure

In a 200 ml four-necked flask were placed 49.53 g (0.240 mol) of 2,6-di-tert-butylphenol (hereinafter abbreviated to “2,6-DBP”), 2.05 g (0.018 mol) of DMi and 40 g of xylene, and the solution was heated until reflux begun. Afterward, azeotropic dehydration was carried out, while 4.41 g (0.054 mol) of a 49 wt % aqueous NaOH solution was added dropwise over 5 hours. Next, 20 g of xylene was added dropwise, and the solution was allowed to mature under the reflux for 2 hours. It was confirmed that a stoichiometric amount of water was distilled. The reaction solution was put in a 300 ml autoclave, heated up to 160° C., and then allowed to absorb a carbon dioxide gas at 6 kg/cm2G, followed by maturation at the same temperature for 5 hours. In this case, a conversion was 90.0%/NaOH. The reaction solution was slowly cooled to 70° C., and then crystallized at 70° C. for 2 hours. The reaction solution was filtered at the same temperature, and then washed three times with 20 g of xylene to obtain wet sodium 3,5-ditert-butyl-4-hydroxybenzoate. According to analysis, the recovery yield of sodium 3,5-di-tert-butyl-4-hydroxybenzoate was 88.4%/NaOH, and any DMi was not detected. It was confirmed that DMi was completely recovered in a filtrate and a wash liquid in the steps of the heating, the filtration and the washing. The wet product was dissolved in 54 g of water at 60° C., and an extraction operation was carried out twice with 18 g of xylene to obtain an aqueous layer. Xylene dissolved in this aqueous layer was distilled off under reduced pressure, and the aqueous layer was added dropwise to 49 g of a 6% sulfuric acid solution over 2 hours to crystallize. The resulting precipitate was filtered, and then washed three times with 12 g of water. Next, wet 3,5-di-tert-butyl-4-hydroxybenzoic acid was taken out, and then dried to obtain 12.0 g of 3,5-di-tert-butyl-4-hydroxybenzoic acid, and a purity was 99.9% or more and a total recovery yield in terms of pure product from the raw material was 88.0%/NaOH.

Workup

  1. customIn a 200 ml four-necked flask were placed
  2. temperatureuntil reflux
  3. additionwas added dropwise over 5 hours
  4. temperaturereflux for 2 hours
  5. distillationwas distilled
  6. customto absorb a carbon dioxide gas at 6 kg/cm2G
  7. temperatureThe reaction solution was slowly cooled to 70° C.
  8. customcrystallized at 70° C. for 2 hours
  9. filtrationThe reaction solution was filtered at the same temperature
  10. washwashed three times with 20 g of xylene

Sources & evidence

ORD record
ord-d4e648820111444aa5b65b4516642a29
Source dataset
uspto-grants-2002_05
Patent number
US06392090B1

Reaction notes

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