Sulfuric Acid → 1,1-Dichloroethane

HRID 1380101Notes

Reaction equation

HRID 1380101 reaction equation
[C:1]1(C)C(S(O)(=O)=O)=CC=CC=1.[C:12]12([CH2:22][S:23]([OH:26])(=[O:25])=[O:24])[C:19]([CH3:21])([CH3:20])[CH:16]([CH2:17][CH2:18]1)[CH2:15][C:13]2=[O:14].FC(F)(F)C(O)=O.CS(O)(=O)=O.S(=O)(=O)(O)O.[CH2:44]([Cl:46])[Cl:45]>COCCOC.C1COCC1.C(Cl)(Cl)Cl>[C:12]12([CH2:22][S:23]([OH:26])(=[O:24])=[O:25])[C:19]([CH3:21])([CH3:20])[CH:16]([CH2:17][CH2:18]1)[CH2:15][C:13]2=[O:14].[Cl:45][CH:44]([Cl:46])[CH3:1]

Participants

11

Reactant 6

HCID 1118Sulfuric AcidHCID 6344Dichloromethane2×HCID 6395Methanesulfonic AcidHCID 6422Trifluoroacetic acidHCID 69252-Methylbenzenesulfonic acidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-

Product 2

HCID 63651,1-DichloroethaneHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Compound 2 is first treated as described above in Method B, Step 1, to obtain an intermediate phenol dihydropyridine which is then treated with about 0.1-0.3 meq (preferably 0.1 meq) of an acid (toluenesulfonic acid, camphorsulfonic acid, trifluoroacetic acid, methanesulfonic acid, sulfuric acid; preferably, camphorsulfonic acid) in a solvent such as CH2Cl2, CHCl3, dichloroethane, THF, DME, or mixtures thereof (preferably methylene chloride) at about 25° to 50° C. for about 2-24 hours to obtain compound 1a.

Sources & evidence

ORD record
ord-21e540b526814508b26cee12aff2f2ed
Source dataset
uspto-grants-1986_04
Patent number
US04579851

Reaction notes

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