Water → HCID 13124210, compound

HRID 2089495Notes

Reaction equation

HRID 2089495 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9]([CH3:15])([CH3:14])[C:10]2=[O:13])=[CH:5][CH:4]=1.[BH4-].[Na+].O>CO.ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9]([CH3:15])([CH3:14])[CH:10]2[OH:13])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 13124206HCID 13124206, compound

Product 1

HCID 13124210HCID 13124210, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphthalen-1-one (1.42 g, 6.81 mmol) in methanol (15 mL) and dichloromethane (5 mL) is added NaBH4 (1.04 g, 27.25 mmol) in one portion. After 15 min, water is added and the organic solvents are evaporated in vacuo. The aqueous layer is extracted with ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered, and concentrated to give 7-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphthalen-1-ol, which is used in the next step without further purification.

Workup

  1. customthe organic solvents are evaporated in vacuo
  2. extractionThe aqueous layer is extracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ecb71eb41e78437c927c801a56f04f02
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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