Hydrochloric Acid → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

HRID 2076421Notes

Reaction equation

HRID 2076421 reaction equation
[OH-:1].[Na+].[CH3:3][C:4]1([CH3:17])[C:13]2[CH:8]([CH2:9][C:10]([CH3:14])=[CH:11][CH:12]=2)[C:7]([CH3:16])([CH3:15])[CH2:6][CH2:5]1.[O-:18][Mn](=O)(=O)=O.[K+].Cl>O.N1C=CC=CC=1>[CH3:3][C:4]1([CH3:17])[CH2:5][CH2:6][C:7]([CH3:16])([CH3:15])[C:8]2[CH:9]=[C:10]([C:14]([OH:18])=[O:1])[CH:11]=[CH:12][C:13]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 86612828HCID 86612828, compound

Product 1

HCID 2276385,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acidYield 57.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
95 °C

Procedure

A three neck round bottom flask (250 ml) equipped with a magnetic stirrer was charged with pyridine (37.5 mL), H2O (12.5 ml) and NaOH (0.39 g, 9.8 mmol). 1,1,4,4,6-Pentamethyltetrahydronaphtalene 1 (1.00 g, 4.9 mmol) and KMnO4 (3.12 g, 19.8 mmol) were added successively. The reaction mixture was stirred and heated at 95° C. for 16 h and cooled to 1° C. using an ice-water bath. HCl (6 N, 100 mL) was added to acidify to pH=1 and the product was extracted with EtOAc (5×100 mL), dried over Na2SO4, filtered to give after evaporation 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid 2 (0.65 g, 57% yield) as a white solid.

Workup

  1. customA three neck round bottom flask (250 ml) equipped with a magnetic stirrer
  2. temperaturecooled to 1° C.
  3. extractionthe product was extracted with EtOAc (5×100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customto give

Sources & evidence

ORD record
ord-e742d88b7a6442f88a82775c0c04d9d5
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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