Hydrochloric Acid → HCID 67202997, compound

HRID 1047658Notes

Reaction equation

CO.C([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[C:20]([N+:31]([O-:33])=[O:32])[CH:19]=2)=[CH:14][CH:13]=1)(=O)C1C=CC=CC=1.[OH-].[Li+].Cl>>[CH3:28][C:27]([CH3:30])([CH3:29])[CH2:26][CH2:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH:16]=[CH:17][C:12]([OH:11])=[CH:13][CH:14]=2)=[CH:19][C:20]=1[N+:31]([O-:33])=[O:32]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 3939Lithium Hydroxide

HCID 67204900HCID 67204900, compound

Product 1

HCID 67202997HCID 67202997, compound

Procedure

In synthesizing the liquid crystal material of Formula 1(10), first, benzoyl chloride was dropped into 4,4′-biphenol pyridine solution, and the resultant was subsequently stirred all night at room temperature. The obtained precipitated substance was filtrated, and subsequently 4′-hydroxy-4-biphenyl benzoate was obtained by column chromatography with the use of silica-gel. Subsequently, 4′-hydroxy-4-biphenyl benzoate was dispersed into acetic acid. Thereafter, while temperature was kept at 15 degree centigrade, nitric acid was dropped into the resultant, water was further added thereto, and the resultant was stirred. The obtained precipitated substance was recrystallized by ethanol and acetic acid, and therefore 4′-hydroxy-3′-nitro-4-biphenyl benzoate was obtained. Subsequently, tetrahydrofuran solution composed of 4′-hydroxy-3′-nitro-4-biphenyl benzoate, triphenyl phosphine, and 3,3-dimethylbutyl-1-ol was put into a flask substituted with argon gas (Ar). Thereafter, azodicarboxylic diethyl tetrahydrofuran solution was dropped into the resultant, which was stirred all night at room temperature. Subsequently, after the solvent was volatilized, by using column chromatography, 4′-(3,3-dimethylbutyloxy)-3′-nitro(1,1′-biphenyl)-4-yl benzoate was obtained. Subsequently, 4′-(3,3-dimethylbutyloxy)-3′-nitro(1,1′-biphenyl)-4-yl benzoate methanol solution was added with lithium hydroxide solution, and the resultant was stirred all night at room temperature. Subsequently, after the solvent was volatilized, neutralization was performed by hydrochloric acid, and a target substance was extracted by ethyl ether. Subsequently, dehydration was performed by magnesium sulfate, and the solvent was volatilized. Thereafter, by using column chromatography, 4′-(3,3-dimethylbutyloxy)-3′-nitro(1,1′-biphenyl)-4-ol was obtained. Subsequently, dichloromethane solution composed of 4′(3,3-dimethlbutyloxy)-3′-nitro(1,1′-biphenyl)-4-ol, p-octyloxybenzoic acid, and 4-dimethylaminepyridine was added to 1-(3-(dimethylamino)-propyl)-3-ethylcarbodimide methiodine, and the resultant was subsequently stirred all night at room temperature. Subsequently, after the solution was washed with water, the resultant was separated and dried over sodium sulfate. Finally, after the solvent was volatilized, the liquid crystal material of Formula 1(10) was obtained by using column chromatography.

Workup

extractiona target substance was extracted by ethyl ether

Sources & evidence

ORD record: ord-57c37672e3fe4dd893be6dc69b758c46
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08570481B2

Reaction notes

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