Formaldehyde → HCID 23021572, compound

2.90 g of 3-cyclopentylphenol was dissolved in 14.5 mL of toluene, to which 0.21 mL of tin tetrachloride and 1.7 mL of tri-n-butylamine were added at room temperature in a stream of nitrogen, and then this mixture was stirred for 30 minutes at room temperature followed by addition thereto of 1.18 g of paraformaldehyde, and this mixture was stirred for 1.5 hours at 80° C. Then, the reaction mixture was cooled to room temperature and poured into water, to which methylene chloride was added, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=10:1] to yield 0.77 g of 4-cyclopentyl-2-hydroxybenzaldehyde as yellow oil.

1. additionwere added at room temperature in a stream of nitrogen
2. additionfollowed by addition
3. temperatureThen, the reaction mixture was cooled to room temperature
4. additionwas added
5. customthe organic phase was separated
6. washAfter the resultant organic phase was washed with water
7. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
8. distillationthe solvent was distilled out under reduced pressure
9. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=10:1]

ORD record

ord-1147e87d9f184ae6bcf70f202cbe577c

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772285B2