Dimethyl Sulfoxide → 5,8-Dihydro-1-naphthyl benzyl ether

HRID 267559

反応式

HRID 267559 の反応式
[C:1]1([OH:11])[C:10]2[CH2:9][CH:8]=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.CS(C)=O.C[O-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[CH2:19]([O:11][C:1]1[C:10]2[CH2:9][CH:8]=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 7498Benzyl BromideHCID 974665,8-Dihydro-1-naphtholHCID 10942334Sodium Methoxide

生成物 1

HCID 203605175,8-Dihydro-1-naphthyl benzyl ether

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 73 g. (0.5 m) of 5,8-dihydro-1-naphthol in 100 ml. DMSO is treated with 0.5 m sodium methoxide. The mixture is cooled in an ice bath and treated dropwise with 0.5 mole benzyl bromide with shaking periodically. The mixture is gradually allowed to warm up to about 45° toward the end of addition. The mixture is stirred 3 hrs. longer, then poured into 1 liter H2O and extracted into ether. Extracts are washed twice with 10% NaOH, dried, taken to dryness leaving almost a quantitative yield of crystalline 5,8-dihydro-1-naphthyl benzyl ether.

後処理

  1. temperatureThe mixture is cooled in an ice bath
  2. temperatureto warm up to about 45° toward the end of addition
  3. stirringThe mixture is stirred 3 hrs
  4. extractionextracted into ether
  5. washExtracts are washed twice with 10% NaOH
  6. customdried

出典と根拠

ORDレコード
ord-9758e78849c448b5a32ec211e23ab811
出典データセット
uspto-grants-1976_03
特許番号
US03943149

関連ノート

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