HCID 12725565, compound → HCID 9989769, compound

HRID 236950Notes

Reaction equation

HRID 236950 reaction equation
[C:1]([C:4]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][CH2:9]2)(=O)[CH3:2]>O1CCOCC1.Cl>[CH2:1]([C:4]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][CH2:9]2)[CH3:2]

Participants

4

Reactant 1

HCID 12725565HCID 12725565, compound

Product 1

HCID 9989769HCID 9989769, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Acetyl-6-hydroxy-1,2,3,4-tetrahydronaphthalene (15.0 g) was heated at reflux in a mixture of dioxan (40 ml) and 50% HCl (50 ml) containing zinc amalgam (16.0 g) for 18 hours. The mixture was cooled, filtered and the filtrate was extracted with ether. The ether extracts were washed with water, dried (MgSO4), filtered and evaporated to dryness leaving a solid which crystallised from petroleum ether (60°-80°) to give 5-ethyl-6-hydroxy-1,2,3,4-tetrahydronaphthalene as pale yellow needles, 13.5 g (97%), mp 94°-5°.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. extractionthe filtrate was extracted with ether
  4. washThe ether extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customleaving a solid which
  9. customcrystallised from petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-9544a0d3f46e432d8bfcc7eeb8e56940
Source dataset
uspto-grants-1979_06
Patent number
US04159273

Reaction notes

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