tert-Butanol → HCID 11770378, compound

HRID 1976860Notes

Reaction equation

HRID 1976860 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:9](=[O:10])[O:8][CH2:7]2)([OH:3])=[O:2].[C:14]1([CH3:24])[CH:19]=CC(S(Cl)(=O)=O)=C[CH:15]=1.C(O)(C)(C)C>N1C=CC=CC=1>[C:14]([O:2][C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:9](=[O:10])[O:8][CH2:7]2)=[O:3])([CH3:24])([CH3:19])[CH3:15]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 73974-Toluenesulfonyl chlorideHCID 785171,3-Dihydro-1-oxoisobenzofuran-5-carboxylic acid

Product 1

HCID 11770378HCID 11770378, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Carboxyphthalid (100 g, 0.56 mole) is suspended in pyridine (1200 mL). p-toluenesulfonyl chloride (211 g, 1.12 mole) is added and the mixture is stirred for 30 minutes at room temperature. Tert.Butanol (54 g, 0.73 mole) is added and the reaction mixture is left at room temperature with efficient stirring for 3 days. The clear solution is poured into ice water and the precipitated crystals are filtered off. The product is recrystallized from 2-propanol (500 mL). Yield: 123 g, 94%. DSC onset: 151.5° C.

Workup

  1. waitthe reaction mixture is left at room temperature
  2. stirringwith efficient stirring for 3 days
  3. filtrationthe precipitated crystals are filtered off
  4. customThe product is recrystallized from 2-propanol (500 mL)
  5. custom151.5° C.

Sources & evidence

ORD record
ord-3e63583961ae4599ab72317e98c150c4
Source dataset
uspto-grants-2001_05
Patent number
US06229026B1

Reaction notes

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