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

HRID 79504

반응식

HRID 79504 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; emulsion) and neutralized with the addition of 1M HCl solution. The aqueous layer was extracted with ethyl acetate (3×), and the organics were combined. The organic layer was washed with water (2×), brine (1×), separated, dried over MgSO4, filtered, and concentrated in vacuo to afford the crude product as an oil. The residue was loaded onto a large fritted 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 an oil (39.4 g, 92%).

후처리

  1. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  2. washThe organic layer was washed with water (2×), brine (1×)
  3. customseparated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford the crude product as an oil
  8. washeluted with 9:1 hexanes
  9. customethyl acetate until the starting material/olefin were collected
  10. washThe plug was then eluted with 1:1 hexanes
  11. washethyl acetate until the pure desired product was eluted completely

출처 및 근거

ORD 기록
ord-f355148a131e46a1adb6b871665d0c23
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841304B2

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