2-Chloroethanol → 2-Chloroethyl 2-hydroxypropanoate

HRID 1656706노트

반응식

HRID 1656706 반응식
[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[Cl:7][CH2:8][CH2:9]O.OS(O)(=O)=O.O>C1(C)C=CC=CC=1>[C:1]([O:6][CH2:9][CH2:8][Cl:7])(=[O:5])[CH:2]([CH3:4])[OH:3]

참가 물질

6

반응물 4

HCID 342-ChloroethanolHCID 612Lactic AcidHCID 962WaterHCID 1118Sulfuric Acid

생성물 1

HCID 189532282-Chloroethyl 2-hydroxypropanoate수율 60%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Lactic acid (74 mL of an 85% aqueous solution, 0.84 mol) and freshly distilled 2-chloroethanol (670 mL, 10.0 mol) were refluxed with 400 mL of toluene and 0.4 mL of conc. H2SO4 until one equivalent of H2O was collected in a Dean-Stark trap. The reaction mixture was cooled to room temperature, diluted with ethyl ether, and washed with a NaHCO3 /NaCl solution. The organic phase was dried with MgSO4, solvent was removed under reduced pressure, and the residue was distilled at 10 mm Hg. A fraction recovered at 95°-100° C./10 mm Hg was redistilled to give 2-chloroethyl lactate as a clear colorless liquid (76.7 g, 60%): b.p. 95° C./10 mm Hg; 1H NMR δ 1.46 (d, 3 H, J=6.9 Hz), δ 2.95 (bs, 1 H), δ 3.72 (t, 2 H, J=5.6 Hz), δ 4.35 (q, 1 H, J=6.9 Hz), δ 4.44 (m, 2 H); 13C NMR20.4, 41.2, 64.8, 66.8, 175.2 ppm; HRMS calcd for C4H5ClO3Tms (M--CH3) 209.0401, obsd 209.0392.

후처리

  1. customwas collected in a Dean-Stark trap
  2. additiondiluted with ethyl ether
  3. washwashed with a NaHCO3 /NaCl solution
  4. dry with materialThe organic phase was dried with MgSO4, solvent
  5. customwas removed under reduced pressure
  6. distillationthe residue was distilled at 10 mm Hg
  7. customA fraction recovered at 95°-100° C./10 mm Hg
  8. distillationwas redistilled

출처 및 근거

ORD 기록
ord-da4d1780d05b4543ad5264243ebad4e8
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05254718

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