Sulfuric Acid → HCID 66823716, compound

HRID 1193218Notes

Reaction equation

HRID 1193218 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[C:10]([CH:18]3[C:20]4([C:24](=[O:25])[C:23]([CH3:27])([CH3:26])[O:22][C:21]4([CH3:29])[CH3:28])[O:19]3)[CH:9]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:17])[F:15])=[C:10]([CH:18]3[C:20](=[O:19])[C:21]([CH3:28])([CH3:29])[O:22][C:23]([CH3:27])([CH3:26])[C:24]3=[O:25])[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86663662HCID 86663662, compound

Product 1

HCID 66823716HCID 66823716, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To an ice-cold solution of crude 2-(4′-chloro-4-trifluoromethylbiphenyl-3-yl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one (2.59 g, 6.12 mmoles) in dichloroethane (25 ml) is added concentrated sulfuric acid (5 ml), followed by stirring at this temperature for 2 hours. The reaction mixture is poured into ice, extracted with dichloromethane (×2), and the combined organics are evaporated under reduced pressure to yield a brown gum. Purification by flash column chromatography (isohexane to 30% ethyl acetate in isohexane as eluant) then reverse phase preparative HPLC affords 4-(4′-chloro-4-trifluoromethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.370 g) as a white solid.

Workup

  1. additionThe reaction mixture is poured into ice
  2. extractionextracted with dichloromethane (×2)
  3. customthe combined organics are evaporated under reduced pressure
  4. customto yield a brown gum
  5. customPurification by flash column chromatography (isohexane to 30% ethyl acetate in isohexane as eluant)

Sources & evidence

ORD record
ord-775a364cb2fb47699f7d0d2c11f54dca
Source dataset
uspto-grants-2014_03
Patent number
US08680299B2

Reaction notes

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