Hydrochloric Acid → HCID 54204419, compound

HRID 976532Notes

Reaction equation

HRID 976532 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 8028TetrahydrofuranSolventHCID 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 tetrahydrofurna 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 adjusted to ph 2 with 6N hydrochlorid 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-d2ef6642613143a2904f5bf703442963
Source dataset
uspto-grants-1997_03
Patent number
US05612381

Reaction notes

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