4-Hydroxybenzaldehyde → p-Octyloxycarbonyloxybenzaldehyde

HRID 1194645

Reaction equation

HRID 1194645 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:12].O.C1(C)C=CC=CC=1>N1C=CC=CC=1>[CH2:14]([O:13][C:11]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)=[O:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 1140TolueneHCID 81956Carbonochloridic acid, octyl ester

Product 1

HCID 13828007p-OctyloxycarbonyloxybenzaldehydeYield 92.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Commercially available 4-hydroxybenzaldehyde (17.8 g, 0.15 mol) was dissolved in dry pyridine (100 ml) and to the solution was dropwise added under cooling, octyl chloroformate (25 g, 0.13 mol), followed by agitating the mixture at 50°-60° C. for about 2 hours, adding water and toluene thereto, sufficiently agitating the mixture, washing the separated toluene layer with 6N-HCl, then 2N-NaOH aqueous solution and further with water until the washing water became neutral, drying the layer with anhydrous sodium sulfate and distilling off toluene to obtain 4-octyloxycarbonyloxybenzaldehyde (33 g, 0.12 mol), dissolving this compound (33 g, 0.12 mol) in acetic acid (90 ml), dropwise adding to the solution, a solution of chromium oxide (25.2 g, 0.25 mol) dissolved in acetic acid (30 ml) and water (20 ml), at about 20° C., heating the mixture up to 40° C., keeping it for 8 hours, placing water therein, filtering off deposited crystals, washing with water and recrystallizing from ethanol to obtain 4-octyloxycarbonyloxybenzoic acid (31 g), adding thereto thionyl chloride (20 g), refluxing the mixture for about 2 hours, and removing excess thionyl chloride under reduced pressure to obtain 4-octyloxycarbonyloxybenzoic chloride (30 g).

Workup

  1. additionwas dropwise added
  2. temperatureunder cooling
  3. stirringsufficiently agitating the mixture
  4. washwashing the separated toluene layer with 6N-HCl
  5. dry with materialdrying the layer with anhydrous sodium sulfate
  6. distillationdistilling off toluene

Sources & evidence

ORD record
ord-2544277e6ff84f2496b3de156a2d0dd7
Source dataset
uspto-grants-1989_03
Patent number
US04816181

Linked notes

Loading…