Lithium Hydroxide → HCID 22484872, compound

HRID 2181166Notes

Reaction equation

HRID 2181166 reaction equation
C([O:3][C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:18]=3)[CH:13]=2)=[CH:7][CH:6]=1)C.[OH-].[Li+]>C1COCC1.CO>[CH2:23]([O:22][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([O:11][C:8]1[CH:7]=[CH:6][C:5]([C:4]([OH:30])=[O:3])=[CH:10][CH:9]=1)[CH:21]=[CH:20]2)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 20781083HCID 20781083, compound

Product 1

HCID 22484872HCID 22484872, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(6-Benzyloxy-2-naphthyloxy)benzoic acid ethyl ester (10.6 g, 26.2 mmol) was dissolved in a 2:1 mixture of THF and methanol (150 ml), added with 4N lithium hydroxide (33 ml) and stirred at room temperature. After completing the reaction, the reaction liquid was adjusted to pH 2 or thereabout with 1N hydrochloric acid, extracted with ethyl acetate, washed with water, dried with magnesium sulfate and concentrated to obtain the subject compound (8.70 g, 23.4 mmol). The result of 1H-NMR was consistent with the above structure.

Workup

  1. customthe reaction
  2. customthe reaction liquid
  3. extractionwith 1N hydrochloric acid, extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b01873913d5641249e8d6625697cae53
Source dataset
uspto-grants-2005_05
Patent number
US06890932B2

Reaction notes

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