Lithium Hydroxide → 4-((5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)sulfonyl)benzoic acid

HRID 1379795Notes

Reaction equation

HRID 1379795 reaction equation
[CH3:1][C:2]1[C:3]([S:16]([C:19]2[CH:29]=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[Li+].[OH-]>O1CCCC1>[CH3:1][C:2]1[C:3]([S:16]([C:19]2[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:28][CH:29]=2)(=[O:17])=[O:18])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10716721HCID 10716721, compound2×

Product 1

HCID 30259354-((5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)sulfonyl)benzoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 50 mg (0.12 mmol) of ethyl 4-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthylsulfonyl)benzoate (Compound 10) in 3.0 mL of tetrahydrofuran was added 1.0 mL of LiOH (1N aqueous solution). The solution was heated at 50° C. for 3 h, cooled to room temperature and concentrated in vacuo. The residue was diluted with brine, acidified using 10% HCl and extracted with ether (2×). The combined ether layers were dried (MgSO4), filtered, and the solvents were removed in vacuo to give the title compound as a white solid (45 mg, 98%):

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with brine
  4. extractionextracted with ether (2×)
  5. dry with materialThe combined ether layers were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-31e1471c47ef4372b1fe19970daf8298
Source dataset
uspto-grants-1997_09
Patent number
US05672710

Reaction notes

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