Diethyl Ether → Methyl 4-iodobenzoate

HRID 1729

반응식

HRID 1729 반응식
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11]COCC.[N+](=C)=[N-]>O1CCCC1>[CH3:11][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 120854-Iodobenzoic acid

생성물 1

HCID 69273Methyl 4-iodobenzoate수율 99.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Fifty (50) mmol (12.4 g) of commercially available 4-iodobenzoic acid was dissolved in 200 ml of tetrahydrofuran and then added to an ether solution containing freshly prepared diazomethane. The excess diazomethane was subsequently consumed by addition of glacial acetic acid and the resultant solution was concentrated in vacuo. The residue thus obtained was partitioned between ethyl acetate and saturated NaHCO3. The layers were separated and the aqueous phase was extracted with 100 ml of ethyl acetate. The organic extracts were combined, dried over Na2SO4, and concentrated in vacuo, yielding 13.01 grams (99.3% yield) of a yellow solid which melted at 111° C.

후처리

  1. customThe excess diazomethane was subsequently consumed by addition of glacial acetic acid
  2. concentrationthe resultant solution was concentrated in vacuo
  3. customThe residue thus obtained
  4. customwas partitioned between ethyl acetate and saturated NaHCO3
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with 100 ml of ethyl acetate
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a23a2974ba3941e79b71f0f690cd1e1b
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726312

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