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

HRID 263319Notes

Reaction equation

HRID 263319 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c4709b6e5231415ea5e7fb2f28fad561
Source dataset
uspto-grants-1979_05
Patent number
US04156789

Reaction notes

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