Hydrochloric Acid → Deltamethrinic acid

HRID 323921Notes

Reaction equation

HRID 323921 reaction equation
[CH3:1][C:2]1([CH3:13])[C@H:7]2[C@@H:3]1[C@H:4]([C:9](Br)([Br:11])[Br:10])[O:5][C:6]2=[O:8].CC1(C)[C@H]2[C@@H]1[C@@H](C(Br)(Br)Br)OC2=O.C(=O)([O-])O.[Na+].C([O-])=O.[Na+].Cl>CO>[Br:10][C:9]([Br:11])=[CH:4][C@H:3]1[C@@H:7]([C:6]([OH:8])=[O:5])[C:2]1([CH3:1])[CH3:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723810Sodium FormateHCID 12525226(1R,4R,5S)-6,6-dimethyl-4-(tribromomethyl)-3-oxabicyclo[3.1.0]hexan-2-oneHCID 57005246(1R,4S,5S)-6,6-dimethyl-4-(tribromomethyl)-3-oxabicyclo[3.1.0]hexan-2-one

Product 1

HCID 10924480Deltamethrinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (1R,4R,5S)-6,6-dimethyl-4-(tribromomethyl)-3-oxabicyclo[3.1.0]hexan-2-one (I, R1=X1=X2=Br) and (1R,4S,5S)-6,6-dimethyl-4-(tribromomethyl)-3-oxabicyclo[3.1.0]hexan-2-one (I, R1=X1=X2=Br), 0.38 g (0.001 mol), is stirred with sodium hydrogen carbonate, 0.126 g (0.0015 mol), sodium formate, 0.27 g (0.004 mol), and Pt(C) 5%, 0.03 g, in about 4 ml of methanol at 50° C. for 5.5 hours. The reaction mixture is acidified with aqueous hydrochloric acid and extracted twice with methyl t-butyl ether which is dried and evaporated. There is obtained 0.28 g of purity 61% (GC, area-%). The retention time is identical to that of II prepared according to Ref.6, and MS (Mass (intensity in % of base peak): 296 (5) M+, 298 (9) (M+2)+, 300 (4) (M+4)+, 255 (24), 253 (45), 251 (23), 219 (100), 217 (98), 201 (18), 199 (22), 197 (13), 174 (29), 172 (33)) is identical to MS of II prepared according to Ref.6.

Workup

  1. extractionextracted twice with methyl t-butyl ether which
  2. customis dried
  3. customevaporated
  4. customThere is obtained 0.28 g of purity 61% (GC, area-%)
  5. customprepared
  6. customprepared

Sources & evidence

ORD record
ord-8e95615b77f94d9faaed30f4af1625d5
Source dataset
uspto-grants-2001_04
Patent number
US06215023B1

Reaction notes

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