Hydrochloric Acid → 1-Hydroxy-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

HRID 2179896Notes

Reaction equation

HRID 2179896 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([O:12][CH3:13])=[CH:8][CH:9]=2)[CH:4]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[O:3]1.[OH-:23].[Na+].Cl>CS(C)=O.CN(C=O)C>[OH:23][C:4]1([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2)[CH2:11][CH:2]([CH3:1])[O:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 224889843-Methyl-1-(4-nitrophenyl)-7-methoxyisochroman

Product 1

HCID 224889831-Hydroxy-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 16 (1.3 g) in 4 ml of DMSO and 24 ml of DMF was cooled to 8-12° C. and air was passed through the mixture. To the solution was added 1.2 ml of 50% aqueous sodium hydroxide in one portion and the resulting mixture was stirred for 5 hours. HCl (1 N) was added, and extracted with ethyl acetate three times. The combined organic phases were washed with water, dried over Na2SO4. Removal of the solvent afforded 17 as a syrup (1.6 g), which was used directly for the next step.

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over Na2SO4
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-8752d79b2a844066842846cd7cee0271
Source dataset
uspto-grants-2005_05
Patent number
US06887867B2

Reaction notes

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