Benzyl Chloride → HCID 15030177, 화합물

HRID 248178

반응식

HRID 248178 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[CH:6]=[CH:5]2.C[O-].[Na+].[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO>[CH3:16][CH:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([O:1][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:3]=2)[CH:8]=1)[C:13]([OH:15])=[O:14]

참가 물질

5

반응물 3

HCID 7503Benzyl ChlorideHCID 162920DesmethylnaproxenHCID 10942334Sodium Methoxide

생성물 1

HCID 15030177HCID 15030177, 화합물수율 38.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 6-hydroxy-α-methyl-2-naphthaleneacetic acid (6.48 g, 30 mmol) in methanol (100 ml) is added sodium methoxide (60 mmol). After 10 minutes the solvent is removed and replaced with dimethylformamide (100 ml). Benzyl chloride (7.6 g, 60 mmol) is then added and the reaction mixture is stirred overnight at room temperature. The reaction is then heated at 150° C. for 1 hour. The solvent is then removed and the residue is partitioned between water and methylene chloride. The organic layer is washed with water, dried over magnesium sulfate and evaporated to 11.5 g of crude product. This crude product is extracted with 100 ml hot hexane which affords 3.5 g of white crystals. A final recrystallization from methanol affords 2.5 g of white crystals of the intermediate ether ester (21% yield, m.p. 76°-78° C.).

후처리

  1. customAfter 10 minutes the solvent is removed
  2. temperatureThe reaction is then heated at 150° C. for 1 hour
  3. customThe solvent is then removed
  4. customthe residue is partitioned between water and methylene chloride
  5. washThe organic layer is washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to 11.5 g of crude product
  8. extractionThis crude product is extracted with 100 ml hot hexane which

출처 및 근거

ORD 기록
ord-a87f303f0be841629e4d49b56aa519a5
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05208344

연결된 노트

불러오는 중…