Hydrochloric Acid → HCID 54204419, compound

HRID 862527Notes

Reaction equation

HRID 862527 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH:19]=[O:20])[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:21][CH2:22][CH2:23][O:24][CH2:25][Mg]Cl.[Cl-].[NH4+].Cl.C(OC(C)C)(C)C>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH:19]([OH:20])[CH2:25][O:24][CH2:23][CH2:22][Cl:21])[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 25517Ammonium ChlorideHCID 53819625HCID 53819625, compoundHCID 178478511HCID 178478511, compound

Product 1

HCID 54204419HCID 54204419, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

6.0 g of 6-benzyloxy-2-naphthaldehyde was dissolved in 60 ml of tetrahydrofuran. The solution was cooled to -30° C. Thereto was dropwise added, in 10 minutes, 30 ml of a tetrahydrofuran solution containing 1.6M of 2-chloroethoxymethylmagnesium chloride. The resulting mixture was stirred for 1 hour with ice cooling. The reaction mixture was added to a mixture of 100 ml of ice water, 100 ml of ethyl acetate and 3.6 g of ammonium chloride. The mixture was adjsuted to pH 2 with 6N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium chloride. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: toluene/ethyl acetate=20/1) to obtain a solid. To the solid was added 10 ml of diisopropyl ether. The resulting mixture was stirred at room temperature for 1 hour. The resulting crystals were collected by filtration and dried to obtain 4.7 g of 1-(6-benzyloxy-2-naphthyl)-2-(2-chloroethoxy)ethanol.

Workup

  1. additionThereto was dropwise added, in 10 minutes
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium chloride
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by column chromatography (eluant: toluene/ethyl acetate=20/1)
  8. customto obtain a solid
  9. stirringThe resulting mixture was stirred at room temperature for 1 hour
  10. filtrationThe resulting crystals were collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-0e8243c0882c4c33ad354ab64d6e768a
Source dataset
uspto-grants-1998_02
Patent number
US05719150

Reaction notes

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