Hydrochloric Acid → Chloro-acetic acid 4-oxo-bicyclo[3.2.1]oct-2-en-2-yl ester

HRID 1909437Notes

Reaction equation

HRID 1909437 reaction equation
[CH:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:9])[CH2:3][C:2]2=[O:10].N1C=CC=CC=1.[Cl:17][CH2:18][C:19](Cl)=[O:20].Cl>ClCCl>[O:9]=[C:4]1[CH:5]2[CH2:8][CH:1]([CH2:7][CH2:6]2)[C:2]([O:10][C:19](=[O:20])[CH2:18][Cl:17])=[CH:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 144686Bicyclo(3.2.1)octane-2,4-dione

Product 1

HCID 86661955Chloro-acetic acid 4-oxo-bicyclo[3.2.1]oct-2-en-2-yl esterYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 250 ml round bottom flask containing the bicyclo[3.2.1]octane-2,4-dione (10 g, 72 mmol) is added dry dichloromethane (100 ml) and pyridine (6.28 g, 87 mmol). To the stirred mixture is added dropwise over a period of 15 minutes the chloroacetyl chloride (9.82 g, 72 mmol) diluted in dichloromethane (100 ml). The reaction mixture is therefore stirred for 2 hours at room temperature. The reaction mixture is therefore poured into 100 ml of aqueous 2N HCl and extracted with ethyl acetate (2×100 ml). The combined organic extracts are dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an orange oil. The crude product is distilled under reduced pressure to give chloro-acetic acid 4-oxo-bicyclo[3.2.1]oct-2-en-2-yl ester (13.4 g).

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. dry with materialThe combined organic extracts are dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto give an orange oil
  6. distillationThe crude product is distilled under reduced pressure

Sources & evidence

ORD record
ord-1f9b69f0caa24a0ba33273a0f6a3bffc
Source dataset
uspto-grants-2013_12
Patent number
US08598365B2

Reaction notes

Loading…