Hydrochloric Acid → HCID 14978057, compound

HRID 266704Notes

Reaction equation

HRID 266704 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.[Ti](Cl)(Cl)(Cl)Cl>[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

6

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 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,4-dihydroxy-5,6,7,8-tetrahydronaphthalene (1.640 g, 0.010 mol) in dichloromethane (50 ml) was added titanium tetrachloride (5.69 g, 0.03 mol). Then 1,1-dichlorodimethyl ether (1.73 g, 0.015 mol) was added dropwise under vigorous stirring and the reaction mixture stirred for another 3 h at room temperature. Finally 5% hydrochloric acid (10 ml) was added under ice-cooling. The organic phase was 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 was crystallized from benzene or alternatively submitted to flash chromatography on silica gel with benzene/ethylacetate 85:15 to afford pure title compound in about 60% yield (1.080 g), mp 145° C.

Workup

  1. stirringthe reaction mixture stirred for another 3 h at room temperature
  2. temperaturecooling
  3. customThe organic phase was 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 was crystallized from benzene

Sources & evidence

ORD record
ord-c2d6df76a09e45a082dfc9bc067df85a
Source dataset
uspto-grants-1997_07
Patent number
US05652250

Reaction notes

Loading…