Hydrochloric Acid → 4-Methylbenzene-1,3-dicarboxylic acid

HRID 2218935

반응식

HRID 2218935 반응식
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].C[Mg+].[Br-].CC[O:17][CH2:18]C.[Li]CCCC.CCCCCC.Cl.C[OH:33]>C1COCC1>[CH3:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[C:18]([OH:17])=[O:33]

참가 물질

9

반응물 7

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3283Diethyl EtherHCID 8058HexaneHCID 821303-Bromo-4-methylbenzoic acidHCID 178418339ButyllithiumHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 5957504-Methylbenzene-1,3-dicarboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To THF (130 ml) solution of 3-bromo-4-methyl-benzoic acid (5.0 g, 23.25 mmol) under nitrogen and cooled to −78° C. (dryice/methanol) was added MeMgBr in ether (3.0 M, 8.5 ml, 25.57 mmol) at such a rate that the temperature did not exceed −75° C. The temperature was then allowed to rise to −60° C. and after gas evolution had ceased, the solution was cooled again to −78° C. BuLi in hexane (1.6 M, 29.06 ml, 46.50 mmol) was then added dropwise such that the temperature did not rise above −75° C. The mixture was then stirred at this temperature for 15 minutes before crushed dryice (4.4 g, 100 mmol) was added. The precipitate was vigorously stirred as the temperature was allowed to freely rise to ambient temperature. The mixture was made acidic using 6 N HCl and the solid material collected filteration, washed with diethyl ether and dried. Recrystallisation from water afforded off-white pure compound (81%) m.p. 296-298° C. (sublimed). NMR conforms to expected structure.

후처리

  1. customdid not exceed −75° C
  2. customto rise to −60° C.
  3. customdid not rise above −75° C
  4. custombefore crushed dryice (4.4 g, 100 mmol)
  5. additionwas added
  6. stirringThe precipitate was vigorously stirred as the temperature
  7. customto freely rise to ambient temperature
  8. customthe solid material collected filteration
  9. washwashed with diethyl ether
  10. customdried
  11. customRecrystallisation from water afforded off-white pure compound (81%) m.p. 296-298° C. (sublimed)

출처 및 근거

ORD 기록
ord-3886f99cec384555968b3816e10cb5c9
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07413727B2

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