Lithium Hydroxide → 2-Carboxy-2-(t-butyl)thiomethyl-indan

HRID 22513Notes

Reaction equation

HRID 22513 reaction equation
[C:1]([C:5]1([CH2:14][S:15][C:16]([CH3:19])([CH3:18])[CH3:17])[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>[C:1]([C:5]1([CH2:14][S:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 158143772-Carbomethoxy-2-(t-butyl)thiomethyl-indan

Product 1

HCID 158143782-Carboxy-2-(t-butyl)thiomethyl-indanYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 2-carbomethoxy-2-(t-butyl)thiomethyl-indan (557 mg, 2.0 mmol) in methanol (15 mL) and add 1N lithium hydroxide (3.5 mL). Warm briefly to effect solution then stir at room temperature under an argon atmosphere for 1 hour. Reflux for 6 hours, concentrate in vacuo to a volume of 3 mL and dilute to a volume of 15 mL with water. Wash with methylene chloride and acidify and aqueous phase with excess 2N hydrochloric acid. After 5 minutes, collect the resulting white precipitate by filtration and dry to give 2-carboxy-2-(t-butyl)thiomethyl-indan (506 mg, 96%); mp 158°-163° C.

Workup

  1. temperatureWarm briefly
  2. temperatureReflux for 6 hours
  3. concentrationconcentrate in vacuo to a volume of 3 mL
  4. additiondilute to a volume of 15 mL with water
  5. washWash with methylene chloride
  6. waitAfter 5 minutes
  7. customcollect the resulting white precipitate
  8. filtrationby filtration
  9. customdry

Sources & evidence

ORD record
ord-4ba9be1396874417906a20ee6aea95bc
Source dataset
uspto-grants-1995_06
Patent number
US05428158

Reaction notes

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