Diethyl Ether → 4-Nitro-o-toluic acid

HRID 1761289노트

반응식

HRID 1761289 반응식
I[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].[C:12](=O)([O-:14])[O-:13].[K+].[K+].C(OCC)C.CCCCCC>O.CN(C)C=O.C(OCC)(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl>[N+:8]([C:7]1[CH:6]=[CH:5][C:4]([C:12]([OH:14])=[O:13])=[C:3]([CH3:11])[CH:2]=1)([O-:10])=[O:9]

참가 물질

9

반응물 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 11430Potassium CarbonateHCID 2347812-Iodo-3-nitrotoluene

생성물 1

HCID 747904-Nitro-o-toluic acid수율 31.2%

시약·촉매·용매 4

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 1.0 g(3.8 mmol) of 2-iodo-nitrotoluene, 2.1 g (15.2 mmol) potassium carbonate and 27 mg (0.038 mmol) of palladium(II) dichloride bis (triphenylphosphine) in a mixture of 5 mL of water and 10 mL of N,N-dimethylformamide. This was placed in a Fisher/Porter bottle under 15 psig of carbon monoxideand heated at 70 C for 16 hours. The solution became homogeneous when heated. The reaction was cooled, diethyl ether and water was added, the organic layer separated and discarded. The aqueous layer was acidified with 1N hydrochloric acid, extracted with ethyl acetate, washed with water, brine, dried over magnesium sulfate, filtered and concentrated to yield 0.5 g of crude material. This dissolved in ethyl acetate, hexane added and the resulting brown solid discarded. The filtrate was concentrated, and then recrystallized from diethyl ether/hexane to afford 215 mg of 4-nitro-2-methylbenzoic acid, m/e=182(M+H).

후처리

  1. temperatureheated at 70 C for 16 hours
  2. temperatureheated
  3. temperatureThe reaction was cooled
  4. customthe organic layer separated
  5. extractionextracted with ethyl acetate
  6. washwashed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield 0.5 g of crude material
  11. concentrationThe filtrate was concentrated
  12. customrecrystallized from diethyl ether/hexane

출처 및 근거

ORD 기록
ord-37ca9aaaaa8a4b0f99b5087adf6a4418
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06846954B2

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