Hydrochloric Acid → HCID 14978057, compound

HRID 1081569Notes

Reaction equation

HRID 1081569 reaction equation
[OH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([OH:12])=[CH:4][CH:3]=1.[CH3:13][O:14]C(Cl)Cl.Cl>ClCCl>[OH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([OH:12])=[CH:4][C:3]=1[CH:13]=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 836221,4-Naphthalenediol, 5,6,7,8-tetrahydro-

Product 1

HCID 14978057HCID 14978057, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,4-dihydroxy-5,6,7,8-tetrahydronaphthalene (164 mg, 1 mmol) in dichloromethane (5 ml) is added titantetrachtoride (569 mg, 3 mmol). Then 1,1-dichlorodimethyl ether (173 mg, 1.5 mmol) is added dropwise under vigorous stirring and the reaction mixture stirred for another 3 h at room temperature. Finally hydrochloric acid 5% (1 ml) is added under ice-cooling. The organic phase is separated and the residual aqueous phase repeatedly extracted with ether. The combined organic phases are washed with saturated saline solution, dried over sodium sulfate and evaporated under vacuum. The residue is crystallized from benzene or alternatively submitted to flash chromatography on silica gel with benzene/ethylacetate 85:15 to afford pure 1,4-dihydroxy-5,6,7,8-tetrahydronaphthalene-2-carboxaldehyde in about 60% yield (108 mg).

Workup

  1. stirringthe reaction mixture stirred for another 3 h at room temperature
  2. temperaturecooling
  3. customThe organic phase is separated
  4. extractionthe residual aqueous phase repeatedly extracted with ether
  5. washThe combined organic phases are washed with saturated saline solution
  6. dry with materialdried over sodium sulfate
  7. customevaporated under vacuum
  8. customThe residue is crystallized from benzene

Sources & evidence

ORD record
ord-591ddb9d725e44d4b4990462e7154725
Source dataset
uspto-grants-1996_12
Patent number
US05587385

Reaction notes

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