Acetyl chloride → HCID 19772508, compound

HRID 1614713Notes

Reaction equation

HRID 1614713 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH:5]12[CH2:11][CH:8]([CH2:9][CH2:10]1)[C:7]1[CH:12]=[CH:13][CH:14]=[CH:15][C:6]2=1.[Cl-].[Al+3].[Cl-].[Cl-].C(=O)(O)[O-].[Na+]>C(=S)=S>[C:1]([CH:9]1[CH:8]2[CH2:11][CH:5]([C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=32)[CH2:10]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 1382721,2,3,4-Tetrahydro-1,4-methanonaphthaleneHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19772508HCID 19772508, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

30 cm3 of acetyl chloride are added to a solution of 30 g of benzonorbornene in 400 cm3 of carbon disulphide and then 10.5 g of anhydrous aluminum chloride are added gradually in small quantities over approximately 2 hours. At this stage, the complete conversion of the starting product is checked by thin-layer chromatography. The reaction mixture is then poured into two litres of ice water and then neutralized with sodium bicarbonate. After three extractions with ether, the ether phase is dried over sodium sulphate and then concentrated. 38 g of an orange oil which corresponds to the expected product are obtained.

Workup

  1. extractionAfter three extractions with ether
  2. dry with materialthe ether phase is dried over sodium sulphate
  3. concentrationconcentrated
  4. customare obtained

Sources & evidence

ORD record
ord-6678837d21604da7beff53638898a47d
Source dataset
uspto-grants-1993_03
Patent number
US05198567

Reaction notes

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