Hydrochloric Acid → 4-(3-Methylbutyl)-4-vinylnaphthalene-1,3(2h,4h)-dione

HRID 494668Notes

Reaction equation

HRID 494668 reaction equation
C[O:2][C:3]1[C:12]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])([CH:13]=[CH2:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:20])[CH:4]=1.[OH-].[Na+].Cl>CO>[CH3:18][CH:17]([CH3:19])[CH2:16][CH2:15][C:12]1([CH:13]=[CH2:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:20])[CH2:4][C:3]1=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688721423-Methoxy-4-(3-methylbutyl)-4-vinylnaphthalen-1(4h)-one

Product 1

HCID 688709774-(3-Methylbutyl)-4-vinylnaphthalene-1,3(2h,4h)-dioneYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Example 181C (42 mg, 0.16 mmol) in methanol (1 mL) was added a solution of 1 N NaOH (0.5 mL, 0.5 mmol). The reaction solution was stirred at 60° C. for 96 h. The solution was cooled to room temperature, acidified with 0.1 N HCl, and extracted with ethyl acetate (3× 1 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (20%-40% ethyl acetate/hexane) afforded product as an off-white solid (24 mg, 60%).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with ethyl acetate (3× 1 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-403d0f3dbba14e529a0a0193c86c82a1
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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