Sodium Bicarbonate → Deltamethrinic acid

HRID 323922Notes

Reaction equation

HRID 323922 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+].[H][H].Cl.C(OC)(C)(C)C>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 516892Sodium BicarbonateHCID 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-oneHCID 86756611tert-butylmethylether HClHCID 178418361HCID 178418361, compound

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, R1X1=X2=Br), 0.75 g (0.002 mol), is stirred with sodium hydrogen carbonate, 0.421 g (0.005 mol), and-Pt(C) 5%, 0.06 g in about 9 ml of methanol at 50° C. with gaseous hydrogen being supplied below the liquid surface. Samples taken out for GC analysis are treated with aqueous hydrochloric acid/methyl t-butyl ether and analysed on GC. Already after 1 hour GC analysis (area-%) shows a content of 42% of II and 34% of unreacted I. Identification of II is effected as shown in Example 1.

Workup

  1. customat 50° C.

Sources & evidence

ORD record
ord-70da23231a9a4571b3c8513fdf8d66f3
Source dataset
uspto-grants-2001_04
Patent number
US06215023B1

Reaction notes

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