Hydrochloric Acid → 4-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzoic acid

HRID 2100686Notes

Reaction equation

HRID 2100686 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[C:21]([CH3:22])=[CH:20][C:19]3[C:18]([CH3:24])([CH3:23])[CH2:17][CH2:16][C:15]([CH3:26])([CH3:25])[C:14]=3[CH:13]=2)=[O:11])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>C1COCC1.CO>[CH3:22][C:21]1[C:12]([C:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:27])=[O:2])=[CH:9][CH:8]=2)=[O:11])=[CH:13][C:14]2[C:15]([CH3:26])([CH3:25])[CH2:16][CH2:17][C:18]([CH3:23])([CH3:24])[C:19]=2[CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11726298Methyl 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzoate

Product 1

HCID 98104314-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalene-2carbonyl)-benzoic acid methyl ester (820 mg, 2.25 mmol) in 10 mL of THF and 10 mL of MeOH was added NaOH (22 mL of 1N solution, 22 mmol). The mixture was stirred at room temperature overnight. The mixture was acidified with HCl (23 mL of 1N solution, 23 mmol). The product was extracted with CH2Cl2 twice and EtOAc twice. The combined organic fraction was dried over Na2SO4, filtered and was used in the next step without purification.

Workup

  1. extractionThe product was extracted with CH2Cl2 twice
  2. dry with materialThe combined organic fraction was dried over Na2SO4
  3. filtrationfiltered
  4. customwas used in the next step without purification

Sources & evidence

ORD record
ord-42f9d335697c4af3a5183ec4382b2ed9
Source dataset
uspto-grants-2009_08
Patent number
US07572816B2

Reaction notes

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