2-(4-Benzyloxy-3-propoxyphenyl)-5,5-dimethyl-1,3-dioxane → HCID 22987076, compound

HRID 987869Notes

Reaction equation

HRID 987869 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[O:20][CH2:19][C:18]([CH3:22])([CH3:21])[CH2:17][O:16]2)=[CH:11][C:10]=1[O:23][CH2:24][CH2:25][CH3:26])C1C=CC=CC=1>[Pd].O1CCCC1>[CH3:21][C:18]1([CH3:22])[CH2:17][O:16][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([O:23][CH2:24][CH2:25][CH3:26])[CH:11]=2)[O:20][CH2:19]1

Participants

4

Reactant 1

HCID 229870842-(4-Benzyloxy-3-propoxyphenyl)-5,5-dimethyl-1,3-dioxane

Product 1

HCID 22987076HCID 22987076, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.07 g (3.00 mmol) of 2-(4-benzyloxy-3-propoxyphenyl)-5,5-dimethyl-1,3-dioxane, 15 ml of tetrahydrofuran and 107 g of 10% palladium/C hydrogenation catalyst was hydrogenated at room temperature. After the absorption of 62.4 ml of hydrogen, the reaction suspension was filtered through Dicalite and evaporated down. Chromatography of the residue over 25 g of silica gel using 19:1 toluene/ethyl acetate gave 790 mg of 4-(5,5-dimethyl-1,3-dioxan-2-yl)-2-propoxyphenol.

Workup

  1. customwas hydrogenated at room temperature
  2. customAfter the absorption of 62.4 ml of hydrogen
  3. filtrationthe reaction suspension was filtered through Dicalite
  4. customevaporated down

Sources & evidence

ORD record
ord-a94e7249634744398b4e399e10a46b1a
Source dataset
uspto-grants-2003_10
Patent number
US06632909B2

Reaction notes

Loading…