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

HRID 263319노트

반응식

HRID 263319 반응식
[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

참가 물질

5

반응물 3

HCID 887Methanol2회HCID 4311764Sodium borohydrideHCID 51035275-Hydroxy-2-tetralone

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c4709b6e5231415ea5e7fb2f28fad561
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04156789

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