Chlorosuccinimide → HCID 66611859, compound

HRID 2204722Notes

Reaction equation

HRID 2204722 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1C(=O)N([Cl:20])C(=O)C1>C(#N)C>[Cl:20][C:9]1[C:10]([CH3:12])=[CH:11][C:2]([OH:1])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

Product 1

HCID 66611859HCID 66611859, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 2-hydroxy-4-methylbenzoate (2 g, 12.04 mmol) in acetonitrile (30 mL) was added NCS (1.688 g, 12.64 mmol). The solution was stirred at 100° C. for 2 hours and then cooled. The solvent was removed in vacuo. The residue was redissolved in DCM (20 mL), washed with water (10 mL) and NaHCO3 solution (15 mL), dried over MgSO4 and the solvent removed in vacuo. Purification by column (Si, Isolute, 5% EtOAc/Cyclohexane) gave the title product as a solid (2.42 g, 100% yield).

Workup

  1. temperaturecooled
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was redissolved in DCM (20 mL)
  4. washwashed with water (10 mL) and NaHCO3 solution (15 mL)
  5. dry with materialdried over MgSO4
  6. customthe solvent removed in vacuo
  7. customPurification by column (Si, Isolute, 5% EtOAc/Cyclohexane)

Sources & evidence

ORD record
ord-5c904f1dcaa04ee9b9def7709add7a7b
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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