Lithium Hydroxide → HCID 59443455, compound

HRID 1035594Notes

Reaction equation

HRID 1035594 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:29])/[CH:7]=[CH:8]/[C:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=3)=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[O:27][CH3:28])C>C1COCC1.O>[CH3:28][O:27][C:10]1[CH:11]=[CH:12][C:13]2[C:18](=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=3)[CH:14]=2)[C:9]=1/[CH:8]=[CH:7]/[C:6]([OH:29])=[O:5]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59443470HCID 59443470, compound

Product 1

HCID 59443455HCID 59443455, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (407.7 mg, 9.94 mmol, 6 eq) is added to a solution, cooled at 0° C., of (E)-3-(2-methoxy-6-(3-methoxyphenyl)naphthalene-1-yl)acrylic acid ethyl ester (600 mg, 1.66 mmol, 1 eq) in a mixture of THF/water 3/1 (20 ml), and the reaction mixture is boiled under reflux over night. The solvent is removed in vacuum on a rotary evaporator, and 2 N HCl is added to the residue. This phase is extracted with dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and concentrated in vacuum on a rotary evaporator. The residual solid is the desired product (quantitative yield, 554 mg).

Workup

  1. temperatureunder reflux over night
  2. customThe solvent is removed in vacuum on a rotary evaporator, and 2 N HCl
  3. additionis added to the residue
  4. extractionThis phase is extracted with dichloromethane
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum on a rotary evaporator

Sources & evidence

ORD record
ord-fb9b9d870c394061a08b1e87220e8c5a
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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