HCID 19787828, compound → HCID 19787831, compound

HRID 1656315Notes

Reaction equation

HRID 1656315 reaction equation
[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([CH2:15][CH2:16][CH2:17][O:18]C2CCCCO2)=[CH:7][C:6]=1[C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:3])[CH3:2]>CO>[C:1]([O:4][C:5]1[C:6]([C:25]([CH3:26])([CH3:27])[CH3:28])=[CH:7][C:8]([CH2:15][CH2:16][CH2:17][OH:18])=[CH:9][C:10]=1[C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 19787828HCID 19787828, compound

Product 1

HCID 19787831HCID 19787831, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 14.6 g (37.38 mmol) of 3-(4-acetoxy-3,5-di-tert-butylphenyl)-l-(tetrahydropyran-2-yloxy)propane in 80 ml of anhydrous methanol is stirred together with 1 g of amberlyst 15 (H+ -form) for 2 hours at 45° C. and maintained at room temperature overnight. After dilution of the suspension with 100 ml of methanol, the catalyst is removed by filtration and the filtrate evaporated at reduced pressure leaving 11.53 g of crude product, which is purified by flashchromatography over silica gel with H/AcOEt 3:1 as the eluent. 6.96 g (61%) of 3-(4-acetoxy-3,5-di-tert-butylphenyl)propanol is isolated from the product-containing fractions as a faintly yellowish oil, which gradually crystallizes upon standing, m.p. 93°-95° C. (C19H30O3 ; F. W. 306.4).

Workup

  1. customAfter dilution of the suspension with 100 ml of methanol, the catalyst is removed by filtration
  2. customthe filtrate evaporated at reduced pressure
  3. customleaving 11.53 g of crude product, which
  4. customis purified by flashchromatography over silica gel with H/AcOEt 3:1 as the eluent

Sources & evidence

ORD record
ord-ef9c067f10394edcad5d731d83365ace
Source dataset
uspto-grants-1993_10
Patent number
US05254549

Reaction notes

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