Benzyl Alcohol → Benzyl mesylate

HRID 483016

반응식

HRID 483016 반응식
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(Cl)Cl>O>[CH3:16][S:17]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:19])=[O:18]

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

생성물 1

HCID 148757Benzyl mesylate수율 85%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
-5 °C

실험 절차

Under nitrogen methylene chloride (1.4 liter), benzyl alcohol (129.6 g., 1.2 moles) and triethylamine (182 g., 1.8 moles) were combined, stirred and cooled to -5° C. in an ice-water-acetone bath. A solution of methanesulfonyl chloride (150 g., 1.31 moles) in 100 ml. of methylene chloride was added over 49 minutes, maintaining the temperature between -5° and 2° C. After stirring for 10 minutes at 0°-2° C., the reaction was diluted with 500 ml. of water, precooled to 5° C. The organic layer was separated, washed 2×500 ml. of cold water, dried over MgSO4, filtered and evaporated in vacuo to yield title product as a light yellow oil [190 g.; 85%, 1H-NMR (CDCl3) delta (ppm): 2.9 (s, 3H), 5.2 (s, 2H), 7.4 (m, 5H); Rf 0.75 (CH2Cl2 )]. This product was refrigerated until used in the next step.

후처리

  1. temperaturemaintaining the temperature between -5° and 2° C
  2. stirringAfter stirring for 10 minutes at 0°-2° C.
  3. additionthe reaction was diluted with 500 ml
  4. customprecooled to 5° C
  5. customThe organic layer was separated
  6. washwashed 2×500 ml
  7. dry with materialof cold water, dried over MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-7ebc7b50d9d84716bee3a49feea9645d
출처 데이터셋
uspto-grants-1986_03
특허 번호
US04576964

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