Hydrochloric Acid → 4-Hydroxy-4-(3-methylbutyl)naphthalene-1,3 (2h,4h)-dione

HRID 2110566Notes

Reaction equation

HRID 2110566 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][C:5]1(C(OC)=O)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[CH2:7][C:6]1=[O:16].Cl.[OH-:23].[Na+]>>[OH:23][C:5]1([CH2:4][CH2:3][CH:2]([CH3:21])[CH3:1])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[CH2:7][C:6]1=[O:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68839914Methyl 1-(3-methylbutyl)-2,4-dioxo-1,2,3,4-tetrahydronaphthalene-1-carboxylate

Product 1

HCID 688422414-Hydroxy-4-(3-methylbutyl)naphthalene-1,3 (2h,4h)-dioneYield 63.2%

Procedure

A solution of Example 2C (1 g, 3.47 mmol) in 1 N NaOH (20.8 mL) was stirred at 40° C. for 4 days. The solution was neutralized to pH 7 with 1 N HCl, extracted with ethyl acetate, and the organic layer was concentrated in vacuo. Column chromatography on silica (7% methanol/dichloromethane) afforded the title compound as a white solid (0.54 g, 63.2%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-fe5f5205acf04872bf7b562b322164ad
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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