HCID 12719792, compound → 1-(3,4-Dichlorophenyl)-3-oxabicyclo[3.1.0]hexane-2,4-dione

HRID 332125Notes

Reaction equation

HRID 332125 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:15]([OH:17])=[O:16])[CH2:11][CH:10]2[C:12]([OH:14])=O)[CH:5]=[CH:6][C:7]=1[Cl:8]>C(Cl)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:11][CH:10]2[C:12](=[O:14])[O:17][C:15]3=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 1

HCID 12719792HCID 12719792, compound

Product 1

HCID 588547251-(3,4-Dichlorophenyl)-3-oxabicyclo[3.1.0]hexane-2,4-dione

Reagents, catalysts & solvents 1

HCID 6367Acetyl chlorideSolvent

Procedure

To a stirred solution of the 1-(3,4-dichlorophenyl)cyclopropane-1,2-dicarboxylic acid (28.3 g) in acetyl chloride (142 ml) was heated to reflux for 3 h, cooled to room temperature and evaporated. The oil was dissolved in toluene (100 ml) and evaporated to dryness. This was then repeated twice before triturating the semi-solid in hexane (100 ml). The solid was filtered off, washed with hexane and pulled dry under a nitrogen atmosphere to give a brown solid, yield=26.7 g (101%); 1HNMR (300 MHz, CDCl3) δ 7.52-7.46 (m, 2H, ArH), 7.27-7.24 (m, 1H, ArH), 3.35-3.30 (m, 1H, CH), 2.13-2.10 (m, 1H, CH), 1.97-1.95 (m, 1H, CH).

Workup

  1. temperatureto reflux for 3 h
  2. customevaporated
  3. dissolutionThe oil was dissolved in toluene (100 ml)
  4. customevaporated to dryness
  5. custombefore triturating the semi-solid in hexane (100 ml)
  6. filtrationThe solid was filtered off
  7. washwashed with hexane
  8. custompulled dry under a nitrogen atmosphere
  9. customto give a brown solid, yield=26.7 g (101%)

Sources & evidence

ORD record
ord-d5096de6b0074360847ee759595073a1
Source dataset
uspto-grants-2014_11
Patent number
US08877798B2

Reaction notes

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