Hydrochloric Acid → HCID 54406817, compound

HRID 1596408Notes

Reaction equation

HRID 1596408 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([Mg]Br)[CH:7]=[CH:8][CH:9]=1)[CH3:2].[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16].Cl>CCOCC>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH:15]([OH:16])[C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[Cl:12])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69962-ChlorobenzaldehydeHCID 178466581HCID 178466581, compound

Product 1

HCID 54406817HCID 54406817, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an ether solution of 3-ethoxyphenylmagnesium bromide [prepared from 3-ethoxybromobenzene (6 g, 30 m mol), magnesium (0.8 g, 33 m mol) and ether (30 ml)], an ether solution (30 ml) of 2-chlorobenzaldehyde (2.8 g, 20 m mol) was added dropwise with stirring and under cooling with ice. After 30 minutes, 1 N hydrochloric acid (50 ml) was added thereto. The ether layer was separated and the aqueous layer was extracted with ether (20 ml). After the combined ether layer was washed with a saturated aqueous solution of sodium chloride (15 ml) and dried, the solvent was distilled off under reduced pressure. The resulting residue was subjected to chromatography on silica gel (60 g) using hexane-ethyl acetate (5:1). The resulting fraction containing the desired compound was distilled to obtain the desired compound (3.4 g, 64%) as a colorless oily material (178-179° C./1 mmHg).

Workup

  1. temperatureunder cooling with ice
  2. customThe ether layer was separated
  3. extractionthe aqueous layer was extracted with ether (20 ml)
  4. washAfter the combined ether layer was washed with a saturated aqueous solution of sodium chloride (15 ml)
  5. customdried
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionThe resulting fraction containing the desired compound
  8. distillationwas distilled

Sources & evidence

ORD record
ord-b1128a264134482d95635ef91dea4da7
Source dataset
uspto-grants-2001_09
Patent number
US06291485B1

Reaction notes

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