Lithium Hydroxide → 2-Carboxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthalene

HRID 1656046Notes

Reaction equation

HRID 1656046 reaction equation
[C:1]([C:5]1([CH2:15][S:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)([O:3]C)=[O:2].[OH-].[Li+]>CO.O>[C:1]([C:5]1([CH2:15][S:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 197899492-Carbomethoxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 197899372-Carboxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthaleneYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dissolve 2-carbomethoxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthalene (2.5 g, 8.6 mmol) in methanol (50 mL) and add 1N lithium hydroxide (15 mL, 15 mmol). Stir at reflux for 12 hours and at room temperature for an additional 12 hours. Dilute with water (10 mL) and concentrate in vacuo to 20 mL. Wash with ethyl ether and acidify the aqueous phase with 2N hydrochloric acid. Extract with methylene chloride (2×25 mL), dry (MgSO4) and evaporate the solvent in vacuo to give the title compound as a crystalline solid (2.37 g, 99%).

Workup

  1. concentrationconcentrate in vacuo to 20 mL
  2. washWash with ethyl ether
  3. extractionExtract with methylene chloride (2×25 mL)
  4. dry with materialdry (MgSO4)
  5. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-10581ad776824abb8e98b36396b8a111
Source dataset
uspto-grants-1993_10
Patent number
US05252601

Reaction notes

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