4-Ethyl-2-(1,3-dioxan-4-ylmethoxy)benzaldehyde → 4-Ethyl-2-(1,3-dioxan-4-ylmethoxy)phenylmethanol

HRID 355273Notes

Reaction equation

HRID 355273 reaction equation
[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][O:14]2)[CH:4]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[C:5]([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][O:14]2)[CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 189416144-Ethyl-2-(1,3-dioxan-4-ylmethoxy)benzaldehyde

Product 1

HCID 189415994-Ethyl-2-(1,3-dioxan-4-ylmethoxy)phenylmethanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Using a Parr hydrogenator, 3.4 grams (0.014 mole) of 4-ethyl-2-(1,3-dioxan-4-ylmethoxy)benzaldehyde in 200 mL of ethanol was hydrogenated in the presence of 5% palladium on carbon for two hours at 50 psi. The yield of subject compound was 2.3 grams, following purification by column chromatography on silica gel. The NMR spectrum was consistent with the proposed structure.

Workup

  1. custompurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-3caf45db9cce48a39b81f70a4721203c
Source dataset
uspto-grants-1998_11
Patent number
USH0001759

Reaction notes

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