Hydrochloric Acid → 2-(3-Methoxyphenoxy)benzaldehyde

HRID 129588Notes

Reaction equation

HRID 129588 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1OCC[O:14]1.Cl>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 151257152-[2-(3-Methoxyphenoxy)phenyl]-1,3-dioxolane

Product 1

HCID 146201522-(3-Methoxyphenoxy)benzaldehydeYield 95.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-[2-(3-Methoxyphenoxy)phenyl]-1,3-dioxolane (32.7 g; 0.12 mol) was stirred in a mixture of water (95 ml) and concentrated hydrochloric acid (5 ml) at ambient temperature for 19 hours. The mixture was extracted with ether (2×60 ml) and the combined ether extracts were washed with saturated aqueous sodium bicarbonate solution (30 ml), water (3×30 ml) and saturated brine (30 ml). The resulting solution was dried, filtered and concentrated to give almost pure 2-(3-methoxyphenoxy)benzaldehyde (A) (26.17 g, 95.4% yield) as an oil. This material was used without purification for the following step. However, an analytical sample was prepared by chromatography using a mixture of ether and hexane as eluant to give an amber oil.

Workup

  1. extractionThe mixture was extracted with ether (2×60 ml)
  2. washthe combined ether extracts were washed with saturated aqueous sodium bicarbonate solution (30 ml), water (3×30 ml) and saturated brine (30 ml)
  3. customThe resulting solution was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-87db1fd682964cc5b173736998adc739
Source dataset
uspto-grants-1995_11
Patent number
US05468857

Reaction notes

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