Lithium Hydroxide → HCID 67419776, compound

HRID 1423906Notes

Reaction equation

HRID 1423906 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Li+].[OH-]>CO.C1COCC1.O>[C:11]([S:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:30])=[O:2])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67422255HCID 67422255, compound

Product 1

HCID 67419776HCID 67419776, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of 2-tritylsulfanyl-benzoic acid methyl ester (9.6 g, 23.4 mmol) and LiOH (4.0 g, 95.2 mmol) in 110 mL of MeOH/THF/H2O (1/2/1) was stirred at rt overnight. The reaction mixture was concentrated to remove most organic solvents and diluted with water (150 mL). The solid was filtered off and the filtrate acidified to pH 4-5 using 3 N HCl and then 1 N HCl. The precipitate was collected by filtration, rinsed with water and then dissolved in hot EtOAc (1 L). After cooling, the organic solution was dried over MgSO4, filtered and concentrated to provide 2-tritylsulfanyl-benzoic acid (6.71 g). MS ESI(−) m/e: 395.12 (M−1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove most organic solvents
  3. additiondiluted with water (150 mL)
  4. filtrationThe solid was filtered off
  5. filtrationThe precipitate was collected by filtration
  6. washrinsed with water
  7. dissolutiondissolved in hot EtOAc (1 L)
  8. temperatureAfter cooling
  9. dry with materialthe organic solution was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-4964156cb1934c3fb6d015c952de4e37
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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