Hydrochloric Acid → HCID 19048895, compound

HRID 1779962Notes

Reaction equation

HRID 1779962 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH:11]=[CH:12]2)=[CH:7][CH:6]=1)=O.Cl>O1CCCC1.C1(C)C=CC=CC=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>[OH:2][CH2:3][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH:11]=[CH:12]2)=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 10058288HCID 10058288, compound

Product 1

HCID 19048895HCID 19048895, compoundYield 88.8%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideSolvent

Procedure

In 80 ml of tetrahydrofuran, 20 g of a 70% toluene solution of sodium bis(2-methoxyethoxy)aluminum hydride was dissolved and cooled with ice. To the solution, 20 ml of a tetrahydrofuran solution containing 10 g of 7-methoxycarbonyl-3,4-dihydronaphthalene was dropwise added and stirred for an hour at room temperature. Successively, 100 ml of a 3N aqueous hydrochloric acid solution was added with caution under ice cooling to make the solution acid, and the organic layer was extracted with ether. The ether solution was dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The concentrated residue was mixed with hexane. Formed crystals were filtered to give 7.56 g of 7-hydroxymethyl-3,4-dihydronaphthalene.

Workup

  1. temperaturecooled with ice
  2. additionwas dropwise added
  3. extractionthe organic layer was extracted with ether
  4. dry with materialThe ether solution was dried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionThe concentrated residue was mixed with hexane
  7. customFormed crystals
  8. filtrationwere filtered

Sources & evidence

ORD record
ord-683b264e26294e1ca9819c8ad0685435
Source dataset
uspto-grants-1997_05
Patent number
US05629321

Reaction notes

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