Hydrochloric Acid → 4-((1E)-2-(5,5,8,8-Tetramethyl-3-(1H-pyrazol-1-ylmethyl)-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl)benzoic acid

HRID 1836865Notes

Reaction equation

HRID 1836865 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]2[C:21]([CH2:22][N:23]3[CH:27]=[CH:26][CH:25]=[N:24]3)=[CH:20][C:19]3[C:18]([CH3:29])([CH3:28])[CH2:17][CH2:16][C:15]([CH3:31])([CH3:30])[C:14]=3[CH:13]=2)=[CH:6][CH:5]=1.[OH-].[Na+].Cl>C(O)C.O>[CH3:28][C:18]1([CH3:29])[CH2:17][CH2:16][C:15]([CH3:30])([CH3:31])[C:14]2[CH:13]=[C:12](/[CH:11]=[CH:10]/[C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:32])=[O:2])=[CH:9][CH:8]=3)[C:21]([CH2:22][N:23]3[CH:27]=[CH:26][CH:25]=[N:24]3)=[CH:20][C:19]1=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69136279HCID 69136279, compound

Product 1

HCID 102952954-((1E)-2-(5,5,8,8-Tetramethyl-3-(1H-pyrazol-1-ylmethyl)-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl)benzoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 27.6 g (64.4 mmol) of methyl-4-[2-(5,5,8,8-tetramethyl-3-pyrazol-1-ylmethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoate and 97 mL (193 mmol) of 2 N sodium hydroxide in 300 mL of ethyl alcohol was heated at reflux. After 1 hour, the reaction mixture was cooled to room temperature and diluted with 900 mL of water. The reaction mixture was acidified with 2 N HCl and the product was isolated by filtration, washed with water and pentane and dried to give 25.9 g (97%) of 4-[(E)-2-(5,5,8,8-tetramethyl-3-pyrazol-1-ylmethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoic acid (m.p.=246.5-248° C.) 6.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customthe product was isolated by filtration
  4. washwashed with water and pentane
  5. customdried

Sources & evidence

ORD record
ord-6ebdea682cea473fbe5f8ee7efef0f00
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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