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

HRID 253499Notes

Reaction equation

HRID 253499 reaction equation
[OH-].[Na+].[CH3:3][NH:4][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>[CH3:3][NH:4][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]([CH3:37])([CH3:36])[CH2:31][CH2:30][C:29]([CH3:39])([CH3:38])[C:28]=2[CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11375470Ethyl 4'-(3-methylaminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

Product 1

HCID 113858944'-(3-Methylaminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylic acidYield 65.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to that of Example 2a, by reaction of 400 mg (10 mmol) of sodium hydroxide with 500 mg (1 mmol) of ethyl 4′-(3-methylaminopropoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate (Example 13a) in 30 ml of tetrahydrofuran. 310 mg of 4′-(3-methylaminopropoxy)-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.=242° C., yield=66%).

Sources & evidence

ORD record
ord-b03a65fef0264cc08e049bfd479ad31d
Source dataset
uspto-grants-2011_01
Patent number
US07872026B2

Reaction notes

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