Methanol → 5,6,7,8-Tetrahydronaphthalene-1,6-diol

HRID 263319ノート

反応式

HRID 263319 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[CH2:7]2.CO.[BH4-].[Na+]>C(O)(=O)C>[C:2]1([OH:1])[C:3]2[CH2:4][CH2:5][CH:6]([OH:12])[CH2:7][C:8]=2[CH:9]=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 887Methanol2 回HCID 4311764Sodium borohydrideHCID 51035275-Hydroxy-2-tetralone

生成物 1

HCID 124457385,6,7,8-Tetrahydronaphthalene-1,6-diol

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A 3.7 g. (0.0235 mole) sample of 5-hydroxy-3,4-dihydro-2(1H)-naphthalenone in 125 ml. of methanol is added to a cooled solution of 1.0 g. (0.025 mole) of sodium borohydride in 25 ml. of methanol. After 150 minutes at 0°, 7.2 g. of acetic acid is added and the solvent removed in vacuo. Partitioning between water and methylene chloride gives 3.54 g. of crude product after further extraction, drying and solvent removal. Recrystallization from hexane-ethyl acetate gives 2.92 g., m.p. 126°-128.5°. (lit. m.p. 127°-128°) JACS, 80, 2887 (1958).

後処理

  1. customthe solvent removed in vacuo
  2. customPartitioning between water and methylene chloride
  3. customgives 3.54 g
  4. extractionof crude product after further extraction
  5. customdrying
  6. customsolvent removal
  7. customRecrystallization from hexane-ethyl acetate
  8. customgives 2.92 g

出典と根拠

ORDレコード
ord-c4709b6e5231415ea5e7fb2f28fad561
出典データセット
uspto-grants-1979_05
特許番号
US04156789

反応ノート

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