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Hydrochloric Acid → Deltamethrinic acid

HRID 323921
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HRID 323921 반응식
[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]
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참가 물질

7

반응물 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

생성물 1

HCID 10924480Deltamethrinic acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8e95615b77f94d9faaed30f4af1625d5
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06215023B1

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