Sulfuric Acid → HCID 13391215, compound

HRID 1604351Notes

Reaction equation

HRID 1604351 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)=[O:7])=[CH:4][CH:3]=1.[CH3:19][Mg]Cl.S(=O)(=O)(O)O.C1(C)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2([CH3:19])[C:8]3[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10](=[O:12])[O:7]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 665642-(4'-Chlorobenzoyl)benzoic acidHCID 178418332HCID 178418332, compound

Product 1

HCID 13391215HCID 13391215, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Over a period of 30 minutes a solution of 130 g of 2-(4-chlorobenzoyl)benzoic acid in 300 ml of anhydrous tetrahydrofuran was added drop-wise under nitrogen to 900 ml of a stirred 3M solution of methylmagnesium chloride in anhydrous tetrahydrofuran. After the addition the reaction mixture was kept at reflux temperature for 1 hour. Afterwards it was cooled in an ice bath to room temperature and 1 L of an aqueous 2N sulfuric acid solution was added slowly, followed by 600 ml of toluene. The organic layer was separated and washed with brine, dried and evaporated in vacuo. Bulb to bulb destination (0.1 mm Hg/160° C.) afforded 60 g of 3-(4-chlorophenyl)-3-methyl-1(3H)-isobenzofuranone as a yellow oil. M.S. (C.I.) (M/Z): 260 [M+H]+.

Workup

  1. additionAfter the addition the reaction mixture
  2. temperatureat reflux temperature for 1 hour
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-633c91bf3c3b452c902db65abb5cb20d
Source dataset
uspto-grants-1999_11
Patent number
US05994366

Reaction notes

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