Sodium Hydroxide → 4'-(3-Dimethylaminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylic acid

HRID 253492Notes

Reaction equation

HRID 253492 reaction equation
[OH-].[Na+].[CH3:3][N:4]([CH3:40])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23]CC)=[O:22])=[CH:17][CH:16]=2)=[CH:11][C:10]=1[C:26]1[CH:35]=[CH:34][C:33]2[C:32]([CH3:37])([CH3:36])[CH2:31][CH2:30][C:29]([CH3:39])([CH3:38])[C:28]=2[CH:27]=1>O1CCCC1>[CH3:40][N:4]([CH3:3])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=2)=[CH:11][C:10]=1[C:26]1[CH:35]=[CH:34][C:33]2[C:32]([CH3:36])([CH3:37])[CH2:31][CH2:30][C:29]([CH3:39])([CH3:38])[C:28]=2[CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11306847Ethyl 4'-(3-dimethylaminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

Product 1

HCID 114658784'-(3-Dimethylaminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylic acidYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to that of Example 2a, by reaction of 1.12 g (28 mmol) of sodium hydroxide with 960 mg (1.87 mmol) of ethyl 4′-(3-dimethylaminopropoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate (Example 7a) in 30 ml of tetrahydrofuran. 820 mg of 4′-(3-dimethylaminopropoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylic acid are obtained in the form of a white solid (m.p.=199° C., yield=90%).

Sources & evidence

ORD record
ord-c7bf7af4141c4f79a9b5aea7f7886c8b
Source dataset
uspto-grants-2011_01
Patent number
US07872026B2

Reaction notes

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