Calcium Hydroxide → 6-Methylphthalide

HRID 1972132

Reaction equation

HRID 1972132 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][O:8][C:9]2=[O:10])=[CH:5][CH:4]=1.[OH-].[Ca+2].[OH-].[H][H]>CO.O1CCOCC1.[Pd]>[CH3:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][O:8][C:9]2=[O:10])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 6093208Calcium HydroxideHCID 151906856-(Bromomethyl)isobenzofuran-1(3H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 6387566-MethylphthalideYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A total of 107 g (472 mmol) of 6-bromomethylphthalide was dissolved in 50 mL of methanol (dioxane was also used in different experiment). The solution was added to a parr bottle with 40 g (540 mmol) of calcium hydroxide and 2 g of 10% Pd/C. The suspension was hydrogenated at 40 psi until no more hydrogen uptake was recorded. All solids were filtered and filtrate was concentrated to a total of 67 g of brown solid in 96% yield. 1H NMR (CDCl3) (300 MHz) δ 2.53 (s, 3H), 5.30 (s, 2H), 7.49 (s 1H), 7.54 (d, 3JHCCH=7.9 Hz, 1H), 7.47 (d, 3JHCCH=7.9 Hz, 1H)

Workup

  1. filtrationAll solids were filtered
  2. concentrationfiltrate was concentrated to a total of 67 g of brown solid in 96% yield

Sources & evidence

ORD record
ord-b7f7538792b344a79181375727b0566d
Source dataset
uspto-grants-2013_04
Patent number
US08431721B2

Linked notes

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