Hydrochloric Acid → 2-Ethyl-4,6-dihydroxybenzaldehyde

HRID 1798026Notes

Reaction equation

HRID 1798026 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[C:7]([OH:9])[CH:8]=1)[CH3:2].[CH:11](OCC)(OCC)[O:12]CC.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[C:5]([OH:10])[C:4]=1[CH:11]=[O:12])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31214Ethyl orthoformateHCID 6451240Aluminum(III) ChlorideHCID 127958985-Ethylbenzene-1,3-diol

Product 1

HCID 579397332-Ethyl-4,6-dihydroxybenzaldehydeYield 38.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 5-ethyl-benzene-1,3-diol (2.17 g, 15.72 mmol) and triethyl orthoformate (23.26 g, 157 mmol) in benzene (40 mL) was added AlCl3 (6.30 g, 47.16 mmol) at 0° C. The reaction mixture was stirred at room temperature for 30 minutes. After cooling to room temperature, the mixture was poured onto ice and acidified with HCl. 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 2-ethyl-4,6-dihydroxy-benzaldehyde (1.0 g, 38%). 1H NMR (400 MHz, CDCl3δ 12.40 (s, 1H), 10.08 (s, 1H), 6.25 (s, 1H), 6.00 (s, 1H), 5.80 (s, 1H), 2.90 (m, 2H), 1.30 (m, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe mixture was poured onto ice
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialthe organic extracts was dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-63175b2c8b5d42268494a87be2578483
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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