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

HRID 1581074Notes

Reaction equation

HRID 1581074 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-078232c6c3bb4ac6ab0addecda83c966
Source dataset
uspto-grants-1976_01
Patent number
US03935267

Reaction notes

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