Hydrochloric Acid → Methyl 2-(4-chlorophenyl)-3-hydroxypropanoate

HRID 82364

반응식

HRID 82364 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH2:13]=[O:14].Cl>CS(C)=O.C[O-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:13][OH:14])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 104196Methyl 4-chlorophenylacetate

생성물 1

HCID 19914733Methyl 2-(4-chlorophenyl)-3-hydroxypropanoate수율 92.2%

시약·촉매·용매 2

HCID 10942334Sodium Methoxide촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

Methyl 2-(4-chlorophenyl)acetate (36.7 g, 199 mmol) and paraformaldehyde (6.27 g, 209 mmol) were dissolved/suspended in DMSO (400 mL) and treated with NaOMe (537 mg, 9.94 mmol). The mixture was allowed to stir at room temperature for 2 hours to completion by TLC analysis of the crude. The reaction was poured into ice-cold water (700 mL; white emulsion) and neutralized with the addition of 1M HCl solution. The aqueous portion was extracted with ethyl acetate (3×), and the organics were combined. The organic portion was washed with water twice, once with brine, separated, dried over MgSO4, filtered, and concentrated in vacuo to afford the crude product as a yellow oil. The residue was loaded onto a large fitted filtered with silica gel and eluted with 9:1 hexanes:ethyl acetate until the starting material/olefin were collected. The plug was then eluted with 1:1 hexanes:ethyl acetate until the pure desired product was eluted completely. The concentrated pure fractions yielded methyl 2-(4-chlorophenyl)-3-hydroxypropanoate as a colorless oil (39.4 g, 92%).

후처리

  1. extractionThe aqueous portion was extracted with ethyl acetate (3×)
  2. washThe organic portion was washed with water twice
  3. customonce with brine, separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford the crude product as a yellow oil
  8. customa large fitted
  9. filtrationfiltered with silica gel
  10. washeluted with 9:1 hexanes
  11. customethyl acetate until the starting material/olefin were collected
  12. washThe plug was then eluted with 1:1 hexanes
  13. washethyl acetate until the pure desired product was eluted completely

출처 및 근거

ORD 기록
ord-3b794dbd2fff401d8ced19f2ec0b62d5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846681B2

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