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

HRID 2078156Notes

Reaction equation

HRID 2078156 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-17954de8d014492eb9326841c6248baf
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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