Benzyl Alcohol → Benzyl (2S)-hydroxy(phenyl)acetate

HRID 261747

반응식

HRID 261747 반응식
[C:1]([OH:11])(=[O:10])[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:1]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:10])[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

참가 물질

5

반응물 3

HCID 244Benzyl AlcoholHCID 6101p-Toluenesulfonic acidHCID 439616(S)-mandelic acid

생성물 1

HCID 667423Benzyl (2S)-hydroxy(phenyl)acetate수율 42%

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
10 °C

실험 절차

L-Mandelic acid (10 g.), 6.91 g. of benzyl alcohol, and 75 mg. of p-toluenesulfonic acid in 70 ml. of benzene was refluxed under a Dean-Stark trap for a total of 28 hours on 4 consecutive days. The crude benzyl ester was obtained by successively concentrating the liquor and cooling it to about 10° C. a number of times. The fractions melting between 97° C. and 105° C. were combined, dissolved in CHCl3 and washed twice with 15-ml. portions of 5% aqueous NaHCO3 solution. After evaporation of the CHCl3, the product was recrystallized from benzene to give benzyl L-mandelate, m.p. 104°-106° C., yield 42%.

후처리

  1. customThe crude benzyl ester was obtained
  2. concentrationby successively concentrating the liquor
  3. custommelting between 97° C. and 105° C.
  4. dissolutiondissolved in CHCl3
  5. washwashed twice with 15-ml
  6. customAfter evaporation of the CHCl3
  7. customthe product was recrystallized from benzene

출처 및 근거

ORD 기록
ord-a6485282a9a34f2983b7b57db745df81
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04152333

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