Sulfuric Acid → Ethyl 7-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate

HRID 1868748Notes

Reaction equation

HRID 1868748 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:23])([CH3:22])[C:9]([CH:11]([C:17](OCC)=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.OS(O)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:17]([OH:18])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9](=[O:10])[C:8]2([CH3:22])[CH3:23])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 67099549Diethyl 2-(2-(3-chlorophenyl)-2-methylpropanoyl)malonate

Product 1

HCID 67099815Ethyl 7-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylateYield 50.9%

Procedure

Diethyl 2-(2-(3-chlorophenyl)-2-methylpropanoyl)malonate (8.76 g, 26 mmol) was added to H2SO4 (60 mL, 710 mmol), and the mixture was stirred at room temperature for 45 minutes. Ice (H2O) was added, and the aqueous mixture was extracted with EtOAc (2×). The combined organic layers were washed with water (2×) and brine, dried (MgSO4), and concentrated in vacuo to give the crude compound as an orange oil. The crude oil was purified by silica flash chromatography (0-50% DCM/hexane) to give the desired compound as a white solid (3.90 g). MS (m/e)=295.1 (M+H)+.

Workup

  1. additionIce (H2O) was added
  2. extractionthe aqueous mixture was extracted with EtOAc (2×)
  3. washThe combined organic layers were washed with water (2×) and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude compound as an orange oil
  7. customThe crude oil was purified by silica flash chromatography (0-50% DCM/hexane)

Sources & evidence

ORD record
ord-353af454a9264410a4ac2609af47f436
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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