Hydrochloric Acid → HCID 15816724, compound

HRID 2392736Notes

Reaction equation

HRID 2392736 reaction equation
[H-].[Na+].O1[C:7]2([CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.Cl[CH2:15][C:16]1C=C[CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1.Cl>CN(C)C=O.[Cl-].[Na+].O1CCCC1>[CH3:23][O:22][C:18]1[CH:19]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][CH:7]1[CH2:8][CH2:9][C:10](=[O:13])[CH2:11][CH2:12]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2×HCID 699943-Methoxybenzyl chlorideHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Product 1

HCID 15816724HCID 15816724, compound

Reagents, catalysts & solvents 3

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent3×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

4.4 g of 60% sodium hydride in mineral oil (0.11 mole) were stirred in 35 ml absolute dimethylformamide under a nitrogen atmosphere. 15.7 g (0.1 mole) 1,4-dioxaspiro[4.5]decan-8-ol were dissolved in 65 ml dimethylformamide. This solution was added drop-wise to the sodium hydride suspension. 16 ml 1-chloromethyl-3-methoxybenzene (0.11 mole), dissolved in 25 ml dimethylformamide, were then added. The mixture was stirred for 30 minutes at 60° C., poured on to ice, extracted with ether and dried over sodium sulphate. After evaporation of the solvent, 29 g of crude product were obtained. This was stirred for 1 hour with a mixture of 190 ml tetrahydrofuran and 50 ml of concentrated hydrochloric acid in order to cleave the acetal. The product was diluted with saturated sodium chloride solution, and the phases were separated, extracted with ether and dried. After removal of the solvent by distillation, compound (8) which was obtained was purified with diisopropyl ether via a silica gel column.

Workup

  1. additionwere then added
  2. additionpoured on to ice
  3. extractionextracted with ether
  4. dry with materialdried over sodium sulphate
  5. customAfter evaporation of the solvent
  6. custom29 g of crude product were obtained
  7. customthe phases were separated
  8. extractionextracted with ether
  9. customdried
  10. customAfter removal of the solvent
  11. distillationby distillation

Sources & evidence

ORD record
ord-d600e710bb574dcabd68ad08dc53077c
Source dataset
uspto-grants-1998_09
Patent number
US05801201

Reaction notes

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