Lithium Hydroxide → HCID 22484872, compound

HRID 480264Notes

Reaction equation

HRID 480264 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-2550fae7d2c44412a26cb9d65d2eea78
Source dataset
uspto-grants-2003_11
Patent number
US06649656B1

Reaction notes

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