Sulfuric Acid → 2-(2'-Chlorophenyl)-1,3-cyclohexanedione

HRID 1706959Notes

Reaction equation

HRID 1706959 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[O:16])[CH2:10][CH2:11][CH2:12][C:13](O)=[O:14].S(=O)(=O)(O)O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:9](=[O:16])[CH2:10][CH2:11][CH2:12][C:13]1=[O:14]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 15595129HCID 15595129, compound

Product 1

HCID 128765992-(2'-Chlorophenyl)-1,3-cyclohexanedioneYield 63.2%

Conditions

Temperature
120 °C

Procedure

A 500 ml round bottom flask was charged with 10.0g (0.0416 mol) of 6-(2'-chlorophenyl)-5-ketohexanoic acid and 100 ml of 72% sulfuric acid. The reaction mixture was stirred and heated to 120° C. for 51/2 hours (oil bath), then poured into 600 ml of an ice water mixture. A tacky, white solid formed, and this was extracted into 300 ml of methylene chloride. The CH2Cl2 solution was washed six times with water, dried over anhydrous MgSO4 and stripped to leave 8.87 g of a tacky, white solid. This material was recrystallized from ethyl acetate to give 5.85 g (63%) of 2-(2'-chlorophenyl)-1, 3-cyclohexanedione as a white, crystalline solid, m.p. 148.5°-149° C.

Workup

  1. customA tacky, white solid formed
  2. extractionthis was extracted into 300 ml of methylene chloride
  3. washThe CH2Cl2 solution was washed six times with water
  4. dry with materialdried over anhydrous MgSO4
  5. customto leave 8.87 g of a tacky, white solid
  6. customThis material was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-97aa6920594d4ecab2a326b54251f0f5
Source dataset
uspto-grants-1980_06
Patent number
US04209532

Reaction notes

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