Hydrochloric Acid → 3-Ethoxy-α-phenylbenzenemethanol

HRID 1596407Notes

Reaction equation

HRID 1596407 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:16])[CH3:10].Cl>CCOCC>[CH2:9]([O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]([OH:16])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 899083-EthoxybenzaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 119485713-Ethoxy-α-phenylbenzenemethanolYield 242.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an ether solution of phenylmagnesium bromide [prepared from bromobenzene (3.69 ml, 35 m mol), magnesium (0.95 g, 39 m mol) and ether (50 ml)], an ether solution (30 ml) of 3-ethoxybenzaldehyde (3.0 g, 20 m mol) was added dropwise thereto with stirring and under cooling with ice. After 30 minutes, 1 N hydrochloric acid (20 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 (100 g) using hexane, and eluted with hexane and then with hexane-ethyl acetate (5:1). The resulting yellow oily material containing the desired compound was distilled to obtain the desired compound (2.9 g, 60%) as a colorless oily material (150-153° C./1-2 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. washeluted with hexane
  8. additionThe resulting yellow oily material containing the desired compound
  9. distillationwas distilled

Sources & evidence

ORD record
ord-929ba8b7f1d84e68b1d17ac221a52019
Source dataset
uspto-grants-2001_09
Patent number
US06291485B1

Reaction notes

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