Hydrochloric Acid → Allyl 4-hydroxymethylbenzoate

HRID 617663Notes

Reaction equation

[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.Cl.[CH2:16](O)[CH:17]=C>>[OH:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH2:12][CH:16]=[CH2:17])=[O:10])=[CH:13][CH:14]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 7858Allyl Alcohol

HCID 24758Sodium hydride

HCID 81325Methyl 4-(hydroxymethyl)benzoate

Product 1

HCID 22392687Allyl 4-hydroxymethylbenzoateYield 93%

Procedure

To an alkoxide solution prepared from sodium hydride (60% in oil, 1.60 g, 40.0 mmol) and allyl alcohol (100 mL) was added methyl 4-hydroxymethylbenzoate (3.32 g, 20.0 mmol) under ice-cooling. The resulting mixture was stirred at room temperature for 6 h, adjusted with 1N hydrochloric acid to pH 3, and then concentrated under reduced pressure. To the residue was added ethyl acetate (150 mL), and the mixture was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was separated and purified by silica gel column chromatography (hexane-ethyl acetate, 5:2) to give 3.59 g (93%) of allyl 4-hydroxymethylbenzoate as a pale-yellow oil.

Workup

temperaturecooling
concentrationconcentrated under reduced pressure
additionTo the residue was added ethyl acetate (150 mL)
washthe mixture was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was separated
custompurified by silica gel column chromatography (hexane-ethyl acetate, 5:2)

Sources & evidence

ORD record: ord-db83d4d35d4149a88a32754fd30c5845
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05948785

Reaction notes

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