Water → HCID 23680094, compound

HRID 1937117Notes

Reaction equation

HRID 1937117 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2].[C:16]1(C)C(C)=CC=CC=1.[OH-:24].[Na+:25].[OH2:26]>>[C:1]([C:9]1[CH:10]=[C:11]([C:16]([O-:26])=[O:24])[C:12]([OH:15])=[CH:13][CH:14]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:2])[CH3:3].[Na+:25]

Participants

5

Reactant 4

HCID 962WaterHCID 7237O-Xylene2×HCID 88144-Tert-octylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 23680094HCID 23680094, compound

Conditions

Temperature
130 °C

Procedure

In a 200 ml four-necked flask were placed 49.53 g (0.240 mol) of 4-tert-octylphenol, 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 130° 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 86.7%/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 5-tert-octylsalicylate. According to analysis, the recovery yield of sodium 5-tert-octylsalicylate was 85.3%/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 3 times with 12 g of water. Next, wet 5-tert-octylsalicylic acid was taken out, and then dried to obtain 11.52 g of 5 tert-octylsalicylic acid. In this case, a purity was 99.9% or more and a total recovery yield in terms of pure product from the raw material was 85.2%/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-0ecd365b66eb4927aa47a0f1f2d83fbb
Source dataset
uspto-grants-2002_05
Patent number
US06392090B1

Reaction notes

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