Lithium hydroxide, monohydrate → HCID 21480673, compound

HRID 1490204Notes

Reaction equation

HRID 1490204 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][C:5]([C:18]([O:20]C)=[O:19])([C:6]4[C:11]3=[CH:10][CH:9]=[C:8]([Cl:17])[CH:7]=4)[C:4]=2[CH:3]=1.O.[OH-].[Li+]>O1CCCC1.CO>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][C:5]([C:18]([OH:20])=[O:19])([C:6]4[C:11]3=[CH:10][CH:9]=[C:8]([Cl:17])[CH:7]=4)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21480654HCID 21480654, compound

Product 1

HCID 21480673HCID 21480673, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 2,7-dichloro-9,10-dihydro-9,10-methano-9-anthracenecarboxylate (described in example 35d) (3.25 g, 10.2 mmol) in tetrahydrofuran/methanol (1:1, 70 mL) was added an aqueous solution (35 mL) of lithium hydroxide monohydrate (4.28 g, 102 mmol, 10 eq). A slight exotherm occurred on addition. The reaction was stirred vigorously for 18 h at room temperature over which time a cloudiness develops. The solvents are removed and replaced with 3N HCl (50 mL) saturated with sodium chloride. The aqueous phase was extracted with ethyl acetate (3×50 mL). Combined organic extracts were dried over anhydrous magnesium sulfate, filtered and reduced to an oil. The procedure yielded 3.11 g (quantitative) of the title compound and did not require addition purification.

Workup

  1. additionA slight exotherm occurred on addition
  2. customThe solvents are removed
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
  4. dry with materialCombined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-1d41748a6e1b4e3ba313179124023c36
Source dataset
uspto-grants-1997_10
Patent number
US05681840

Reaction notes

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