Hydrochloric Acid → HCID 14978057, compound

HRID 1684099Notes

Reaction equation

HRID 1684099 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 titantetrachloride (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-a0edc5942ed74987a8e21ef16f7679fe
Source dataset
uspto-grants-1997_06
Patent number
US05639884

Reaction notes

Loading…