3',5'-Dihydroxyacetophenone → 5-Ethylbenzene-1,3-diol

HRID 1798025Notes

Reaction equation

HRID 1798025 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH3:10])[CH:5]=[C:6]([OH:8])[CH:7]=1>Cl.O.[Pd]>[CH2:9]([C:4]1[CH:5]=[C:6]([OH:8])[CH:7]=[C:2]([OH:1])[CH:3]=1)[CH3:10]

Participants

4

Reactant 1

HCID 1039933',5'-Dihydroxyacetophenone

Product 1

HCID 127958985-Ethylbenzene-1,3-diolYield 52.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21885828Hydrate;hydrochlorideSolvent

Procedure

A mixture of 1-(3,5-dihydroxy-phenyl)-ethanone (5 g, 32.89 mmol), 10% Pd—C (1 g) in 4% HCl—H2O (100 mL) was hydrogenated at 1 atmosphere for 16 hours. The mixture was extracted with EtOAc and the organic extracts was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 5-ethyl-benzene-1,3-diol (2.37 g, 52%). 1H NMR (400 MHz, CDCl3δ 6.26 (s, 2H), 6.20 (s, 1H), 4.78 (s, 2H), 2.55 (m, 2H), 1.20 (m, 3H).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialthe organic extracts was dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-6f502665671c4d1a93e86c2c7d3b4f6d
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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