Benzyl Chloride → 4-(Benzyloxy)naphthalen-1-ol

HRID 2247845

反応式

HRID 2247845 の反応式
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[K+].[CH2:23](Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[CH2:23]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

6

反応物 4

HCID 7503Benzyl ChlorideHCID 113051,4-NaphthalenediolHCID 14797Potassium HydroxideHCID 24489Sodium Dithionite

生成物 1

HCID 5629374-(Benzyloxy)naphthalen-1-ol

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

23.7 g. (0.147 mole) 1,4-Dihydroxynaphthalene (purified by shaking an ethereal solution thereof with sodium dithionite solution) are dissolved in 200 ml. acetone. After adding 20.3 g. (0.147 mole) of pulverised potassium hydroxide and heating to reflux temperature, 18.6 g. (16.9 ml.) benzyl chloride are added dropwise thereto in the course of 60 minutes. The reaction mixture is thereafter heated under reflux for 4 hours while stirring, evaporated and the residue is mixed with 100 ml. water and extracted with diethyl ether. The ethereal solution is dried with anhydrous magnesium sulphate, filtered and evaporated. The tar-like residue is extracted with cyclohexane. The combined extracts are cooled, considerable amounts of a tarry product thereby first separating out. Thereafter, the pure compound crystallises out. It is washed with cyclohexane and dried. Yield 4.3 g. (11.9% of theory); m.p. 118°-119° C.

後処理

  1. additionAfter adding 20.3 g
  2. temperatureto reflux temperature, 18.6 g
  3. customin the course of 60 minutes
  4. temperatureThe reaction mixture is thereafter heated
  5. temperatureunder reflux for 4 hours
  6. stirringwhile stirring
  7. customevaporated
  8. additionthe residue is mixed with 100 ml
  9. extractionwater and extracted with diethyl ether
  10. dry with materialThe ethereal solution is dried with anhydrous magnesium sulphate
  11. filtrationfiltered
  12. customevaporated
  13. extractionThe tar-like residue is extracted with cyclohexane
  14. temperatureThe combined extracts are cooled
  15. customconsiderable amounts of a tarry product thereby first separating out
  16. customThereafter, the pure compound crystallises out
  17. washIt is washed with cyclohexane
  18. customdried

出典と根拠

ORDレコード
ord-3dbb469d4090486a9073712ff1576cff
出典データセット
uspto-grants-1991_08
特許番号
US05037828

関連ノート

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