Toluene → 2,6-Di-tert-butyl-4-(5,5-dimethyl-1,3-dioxan-2-yl)phenol

HRID 1605036Notes

Reaction equation

HRID 1605036 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH3:18][C:19]([CH3:24])([CH2:22]O)[CH2:20][OH:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C.O>[OH:13][C:12]1[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]([CH:8]2[O:21][CH2:20][C:19]([CH3:24])([CH3:22])[CH2:18][O:9]2)=[CH:10][C:11]=1[C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 1140TolueneHCID 31344Neopentyl glycolHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 125891522,6-Di-tert-butyl-4-(5,5-dimethyl-1,3-dioxan-2-yl)phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 46.9 parts of 3,5-di-tert.butyl-4-hydroxybenzaldehyde, 21 parts of 2,2-dimethyl-1,3-propane diol and 0.5 parts of 4-toluene-sulphonic acid hydrate in 300 parts of toluene is raised to boiling temperature and reacted with removal of the water of reaction in a separator. After reaction for 6 hours, 85 parts of ethyl acetate are added. The reaction solution is dried over potassium carbonate and the solvent distilled, after which 60 parts of the crude product are obtained. This is recrystallized from hexane to give 2-(4'-hydroxy-3',5'-di-tert.butyl phenyl)-5,5-dimethyl-1,3-dioxane of formula IV, ##SPC3##

Workup

  1. customAfter reaction for 6 hours
  2. dry with materialThe reaction solution is dried over potassium carbonate
  3. distillationthe solvent distilled
  4. customafter which 60 parts of the crude product are obtained
  5. customThis is recrystallized from hexane

Sources & evidence

ORD record
ord-a271ac2087ac406b80089468129ce834
Source dataset
uspto-grants-1976_04
Patent number
US03948946

Reaction notes

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