Tetrahydrofuran → HCID 85906473, compound

HRID 719576Notes

Reaction equation

HRID 719576 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].C1COCC1.[OH:18][C:19]1[CH:29]=[CH:28][CH:27]=[C:21]2[C:22]([O:24][C:25](=[O:26])[C:20]=12)=[O:23]>CCOCC>[CH3:8][S:9]([O:18][C:19]1[CH:29]=[CH:28][CH:27]=[C:21]2[C:22]([O:24][C:25](=[O:26])[C:20]=12)=[O:23])(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 965803-Hydroxyphthalic anhydride

Product 1

HCID 85906473HCID 85906473, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Triethylamine (0.83 g) and methanesulfonyl chloride (0.89 g) were added to a THF solution (10 mL) of 3-hydroxyphthalic anhydride (1.22 g) under ice cooling and the mixture was stirred at room temperature for 8 hours. After finishing the reaction, ether (20 mL) was added and the mixture was washed consecutively with water and saturated aqueous solution of sodium chloride and dried with anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the crude product was washed with a mixed solvent of ether and n-hexane to obtain 3-methanesulfonyloxyphthalic anhydride (1.75 g) having the melting point of 134–140° C.

Workup

  1. additionwas added
  2. washthe mixture was washed consecutively with water and saturated aqueous solution of sodium chloride
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. washthe crude product was washed with a mixed solvent of ether and n-hexane

Sources & evidence

ORD record
ord-1b0eb572ad354337b809740838d237d0
Source dataset
uspto-grants-2006_11
Patent number
US07132455B2

Reaction notes

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