Hydrochloric Acid → 7-Hydroxy-6-methoxy-1-tetralone

HRID 1594776Notes

Reaction equation

HRID 1594776 reaction equation
O.C(=O)(O)[O-].[Na+].C([O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][CH2:17][C:18]2=[O:21])=[CH:13][C:12]=1[O:22][CH3:23])(=O)C.Cl>CO>[CH3:23][O:22][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:11]=1[OH:10])[C:18](=[O:21])[CH2:17][CH2:16][CH2:15]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 21706781HCID 21706781, compound

Product 1

HCID 3168407-Hydroxy-6-methoxy-1-tetraloneYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

3.5 mL of water and then 3.5 mL of saturated aqueous sodium bicarbonate was added to 117 mg of 7-acetoxy-6-methoxytetralin- 1-one dissolved in 7 mL of methanol. The resulting solution was stirred under nitrogen at 25° C. for 17 hours. Thereafter the solution was acidified with aqueous hydrogen chloride and extracted five times with 6 mL portions of methylene chloride. The combined methylene chloride extracts were washed once with brine and dried over anhydrous magnesium sulfate. The dried extract was separated by filtration and the methylene chloride was removed from the filtrate by evaporation at reduced atmospheric pressure and gave 94 mg of 6-methoxy-7-hydroxytetralin-1-one having m.p. 151-152° C.

Workup

  1. extractionextracted five times with 6 mL portions of methylene chloride
  2. washThe combined methylene chloride extracts were washed once with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. extractionThe dried extract
  5. customwas separated by filtration
  6. customthe methylene chloride was removed from the filtrate by evaporation at reduced atmospheric pressure

Sources & evidence

ORD record
ord-42d556f317594c88847f0d8bf456bc3a
Source dataset
uspto-grants-2001_09
Patent number
US06284789B1

Reaction notes

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