Hydrochloric Acid → 2,6-DI-Tert-butyl-4-hydroxyphenyl acetate

HRID 23806Notes

Reaction equation

HRID 23806 reaction equation
[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([O:15]C(=O)C)=[CH:7][C:6]=1[C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:3])[CH3:2].[OH-].[K+].O.Cl>CO>[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:13])([CH3:12])[CH3:14])=[CH:9][C:8]([OH:15])=[CH:7][C:6]=1[C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 126344621,4-Diacetoxy-2,6-di-tert-butylbenzene

Product 1

HCID 111399982,6-DI-Tert-butyl-4-hydroxyphenyl acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

The 1,4-diacetoxy-2,6-di-tert-butylbenzene obtained in Example 11 was dissolved in 60 mL of methanol and the solution was cooled to 20° C.; after adding 3.30 g (50.1 mmol) of potassium hydroxide, the mixture was stirred for 1.5 hours. The mixture was cooled to 10˜15° C. and then 30 mL of water and 12.5 mL of 6 N hydrochloric acid were gradually added. The solution was cooled to 5° C. and stirred for 0.5 hours. The crystal was centrifuged, washed with 10 mL of a methanol/water mixed solvent (methanol/water=1/1) and dried with a through-flow dryer (parallel flow) overnight at 50° C. to give 10.97 g of 4-acetoxy-3,5-di-tert-butylphenol (91.4% in yield from the 2,6-di-tert-butyl-1,4-benzoquinone of Example 10).

Workup

  1. temperatureThe mixture was cooled to 10˜15° C.
  2. temperatureThe solution was cooled to 5° C.
  3. stirringstirred for 0.5 hours
  4. washwashed with 10 mL of a methanol/water mixed solvent (methanol/water=1/1)
  5. customdried with a through-flow dryer (parallel flow) overnight at 50° C.

Sources & evidence

ORD record
ord-471c1615ca10445aa77527d506aac0b5
Source dataset
uspto-grants-2005_02
Patent number
US06852867B2

Reaction notes

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