Carbon Dioxide → 3.5-Diethyl-4-methoxybenzoic acid

HRID 1067360노트

반응식

HRID 1067360 반응식
Br[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([O:10][CH3:11])=[C:4]([CH2:12][CH3:13])[CH:3]=1.C([Li])CCC.[C:19](=[O:21])=[O:20]>C1COCC1.CCOC(C)=O>[CH2:12]([C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH2:8][CH3:9])[C:5]=1[O:10][CH3:11])[C:19]([OH:21])=[O:20])[CH3:13]

참가 물질

6

반응물 3

HCID 280Carbon DioxideHCID 234456364-Bromo-2,6-diethylanisoleHCID 178418339Butyllithium

생성물 1

HCID 234456633.5-Diethyl-4-methoxybenzoic acid수율 66%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

At −78° C., to a stirred solution of 4-bromo-2,6-diethylanisole (12.0 g, 49.4 mmol) in THF (329 mL) was added dropwise n-butyllithium (27.2 mL, 43.5 mmol). After 3 h, the reaction was poured into crushed dry ice and allowed to warm to ambient temperature. The reaction mixture was diluted with EtOAc, concentrated, suspended in H2O, acidified (pH 1), filtered and the collected solids washed with H2O. The crude product was slurried in hexane (15 mL), collected by filtration and dried to give 6.76 g (66%) of the title compound. 1H NMR: consistent. IR (KBr) consistent. mass spectrum (EI), m/z 208 (M+). Anal. Calcd. for C12H16O3: C, 69.21; H, 7.74; N, 0.00. Found: C, 69.28; H, 7.49; N, 0.07.

후처리

  1. additionthe reaction was poured
  2. concentrationconcentrated
  3. filtrationfiltered
  4. washthe collected solids washed with H2O
  5. filtrationcollected by filtration
  6. customdried

출처 및 근거

ORD 기록
ord-57f4258ce5eb4bd1a4b8a7ac790502e2
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248764B1

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