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

HRID 45909Notes

Reaction equation

HRID 45909 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-9f2baa41f5394f648cf574a825322f83
Source dataset
uspto-grants-2013_09
Patent number
US08541594B2

Reaction notes

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