5-Methoxytetralone → 5-Methoxy-1,2,3,4-tetrahydro-1-naphthol

HRID 2089468Notes

Reaction equation

HRID 2089468 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:13].[BH4-].[Na+]>CO.ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH:8]2[OH:13]

Participants

5

Reactant 2

HCID 366205-MethoxytetraloneHCID 4311764Sodium borohydride

Product 1

HCID 44341555-Methoxy-1,2,3,4-tetrahydro-1-naphthol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methoxy-3,4-dihydro-2H-naphthalen-1-one (CAS#33892-75-0, 10 g, 5.67 mmol) in methanol (40 mL) and dichloromethane (5 mL) at 0° C. is added sodium borohydride (0.579 g, 8.51 mmol) in one portion. The cooling bath is removed and after 1.5 hours, the mixture is poured into water (75 mL) and the volatile organics are removed in vacuo. Extraction with dichloromethane, drying over sodium sulfate, filtering through a cotton plug and concentration affords 5-methoxy-1,2,3,4-tetrahydro-naphthalen-1-ol, which is used in the next step without further purification.

Workup

  1. customThe cooling bath is removed and after 1.5 hours
  2. additionthe mixture is poured into water (75 mL)
  3. customthe volatile organics are removed in vacuo
  4. extractionExtraction with dichloromethane
  5. dry with materialdrying over sodium sulfate
  6. filtrationfiltering through a cotton plug and concentration

Sources & evidence

ORD record
ord-53056a9e04674280b7e2d40ffa2d5292
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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