Hydrochloric Acid → 1-(4'-fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol

HRID 990283Notes

Reaction equation

HRID 990283 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:27]=[CH:26][C:11]([C:12]([C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][C:15]=2[C:23](O)=[O:24])=O)=[CH:10][CH:9]=1.Cl>C1COCC1>[F:7][C:8]1[CH:27]=[CH:26][C:11]([CH:12]2[C:14]3[C:15](=[CH:16][C:17]([CH2:18][OH:19])=[CH:21][CH:22]=3)[CH2:23][O:24]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 98355864-(4-Fluorobenzoyl)isophthalic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 99211661-(4'-fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanolYield 8.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (1.0 g) dispersed in THF (10 ml) was added dropwise at room temperature a solution of 4-(4′-fluorobenzoyl)isophthalic acid (3.0 g) in THF (30 ml), and the mixture was stirred for 10 hr. To the reduced reaction mixture was added 10% hydrochloric acid (10 ml) and the mixture was passed through celite. THF was evaporated under reduced pressure, and 85% phosphoric acid (10 g) was added. The mixture was stirred at 60° C. for 5 hr. To the reaction mixture was added water (50 ml) and the resulting crystals were collected by filtration and dried. The objective compound was separated by silica gel column chromatography to give 1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol (0.21 g, 8%). The various spectrum data of the crystals were the same as those obtained in Example 12

Workup

  1. customTHF was evaporated under reduced pressure, and 85% phosphoric acid (10 g)
  2. additionwas added
  3. stirringThe mixture was stirred at 60° C. for 5 hr
  4. additionTo the reaction mixture was added water (50 ml)
  5. filtrationthe resulting crystals were collected by filtration
  6. customdried
  7. customThe objective compound was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-57f5dfb37f2047c3b37a1074575d422f
Source dataset
uspto-grants-2002_10
Patent number
US06458975B1

Reaction notes

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