4-Hydroxybenzaldehyde → Octanoic acid, 4-formylphenyl ester

Commercially available p-hydroxybenzaldehyde (50 g) was dissolved in pyridine (400 ml), followed by dropwise adding octanoyl chloride (80 g) under ice cooling, allowing the mixture to stand overnight, adding toluene (300 ml) and 6N hydrochloric acid, separating the solution, further washing with an aqueous solution of 2N NaOH, washing with water, drying and distilling off toluene to obtain a raw product, which was then distilled under reduced pressure to obtain p-octanoyloxybenzaldehyde (b.p. 174°~7° C./7 mmHg) (58.2 g). This product was dissolved in acetic acid (80 ml), followed by dropwise adding to the solution, a mixed solution of chromium trioxide (23.4 g), water (25 ml) and acetic acid (48 ml), stirring at room temperature for 4 hours, pouring on ice, separating solids by filtering, dissolving them in ethanol (300 ml), adding active carbon, shaking, filtering on heating, ice cooling, filtering crystals and recrystallizing from ethanol (300 ml) to obtain p-octanoyloxybenzoic acid (35 g). M.P.: 151° C. This product (5 g) and oxalic acid chloride (7.2 g) were heated on a water bath at 60° C., followed by allowing the reaction mixture to stand overnight, and distilling off excess oxalic acid chloride in vacuo to obtain p-octanoyloxybenzoyl chloride (5 g). This product was used in the following step without purification.

1. customseparating the solution
2. washfurther washing with an aqueous solution of 2N NaOH
3. washwashing with water
4. customdrying
5. distillationdistilling off toluene
6. customto obtain a raw product, which
7. distillationwas then distilled under reduced pressure

ORD record

ord-47e0f134ae114eaf88f2ce7bbf06fe6e

Source dataset

uspto-grants-1988_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04737313