3,4-Dihydro-6,7-dimethoxy-1(2H)-naphthalenone → 6,7-Dimethoxy-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 2175704Notes

Reaction equation

HRID 2175704 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]2.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([OH:15])[CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 2668163,4-Dihydro-6,7-dimethoxy-1(2H)-naphthalenoneHCID 4311764Sodium borohydride

Product 1

HCID 627354556,7-Dimethoxy-1,2,3,4-tetrahydronaphthalen-1-olYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one (3.09 g, mmol) in MeOH (50 mL) was added NaBH4 (680 mg, 18 mmol) portion wise over 0.5 hour. The resulting mixture was stirred at room temperature overnight. The reaction was quenched with 1N HCl, diluted with water and extracted with DCM. The combined organic phase was washed with brine, dried over sodium sulfate and the solvent was removed under reduced pressure to afford 6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-1-ol as a yellow oil (2.9 g, 93%). LC-MS (ES-API); rt 7.96 min; m/z calculated for C12H16O3 [M+Na]+ 231.1, found 231.1.

Workup

  1. customThe reaction was quenched with 1N HCl
  2. additiondiluted with water
  3. extractionextracted with DCM
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-329be3ed71694273b60b9bf989828d65
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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