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

HRID 253494Notes

Reaction equation

HRID 253494 reaction equation
[OH-].[Na+].[CH2:3]([NH:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25]CC)=[O:24])=[CH:19][CH:18]=2)=[CH:13][C:12]=1[C:28]1[CH:37]=[CH:36][C:35]2[C:34]([CH3:39])([CH3:38])[CH2:33][CH2:32][C:31]([CH3:41])([CH3:40])[C:30]=2[CH:29]=1)[CH2:4][CH3:5]>O1CCCC1>[CH2:3]([NH:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][CH:18]=2)=[CH:13][C:12]=1[C:28]1[CH:37]=[CH:36][C:35]2[C:34]([CH3:39])([CH3:38])[CH2:33][CH2:32][C:31]([CH3:40])([CH3:41])[C:30]=2[CH:29]=1)[CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11455315Ethyl 4'-(3-propylaminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

Product 1

HCID 113754694'-(3-Propylaminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylic acidYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to that of Example 2a, by reaction of 584 mg (14.6 mmol) of sodium hydroxide with 770 mg (1.46 mmol) of ethyl 4′-(3-propylaminopropoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate (Example 9a) in 30 ml of tetrahydrofuran. 470 mg of 4′-(3-propylaminopropoxy)-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.=226° C., yield=64%).

Sources & evidence

ORD record
ord-f912166bf6ae4c7e8f89b6b0e014a23d
Source dataset
uspto-grants-2011_01
Patent number
US07872026B2

Reaction notes

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