Sulfuric Acid → HCID 67100082, compound

HRID 1868856Notes

Reaction equation

HRID 1868856 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.OS(O)(=O)=O.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([CH3:42])([CH3:41])[C:28]([CH:30]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:31]([O:33]CC)=O)=[O:29]>>[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:22]=1[C:27]([CH3:42])([CH3:41])[C:28](=[O:29])[C:30]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:31]2[OH:33]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14812Phosphorus oxide (P4O10)HCID 67099724HCID 67099724, compound

Product 1

HCID 67100082HCID 67100082, compoundYield 28.3%

Procedure

P2O5 (19.0 g, 134 mmol) was treated with concentrated H2SO4 (17.1 mL, 308 mmol) at 0° C., and the resulting mixture was stirred for 30 minutes. Diethyl 2-(2-(2-chlorophenyl)-2-methylpropanoyl)malonate (1.500 g, 3.83 mmol) was added, and the mixture was stirred at 25° C. for 1 hour. The solution was quenched with ice, and, on melting, was extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over MgSO4, and concentrated and dried in vacuo to give ethyl 8-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (0.320 g). MS m/e=295 (M+H)+.

Workup

  1. stirringthe mixture was stirred at 25° C. for 1 hour
  2. customThe solution was quenched with ice
  3. extractionwas extracted with EtOAc (3×100 mL)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-96394cbb7e2549e08b53495cf26bc2cd
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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