Hydrochloric Acid → Octyl 4-formylbenzoate

HRID 648873Notes

Reaction equation

HRID 648873 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:12]([OH:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].Cl>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH2:12]([O:20][C:1]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)=[O:10])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9571-OctanolHCID 124246204-Formylbenzoyl chloride

Product 1

HCID 13404982Octyl 4-formylbenzoateYield 70.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

Next, a solution of the above terephthalaldehydic acid chloride (20 g) dissolved in toluene (100 ml) was dropwise added to a solution of 1-octanol (20 g) dissolved in pyridine (150 ml), followed by heating the mixture on a water bath at 60° C. with stirring, allowing to stand overnight, thereafter adding toluene (500 ml), adding 6N hydrochloric acid, separating the liquid layer, washing with an aqueous solution of 2N NaOH, washing with water, drying, distilling off toluene, and further distilling under reduced pressure to obtain p-octyloxycarbonylbenzaldehyde (166°~167° C./4 mmHg) (22 g).

Workup

  1. customseparating the liquid layer
  2. washwashing with an aqueous solution of 2N NaOH
  3. washwashing with water
  4. customdrying
  5. distillationdistilling off toluene
  6. distillationfurther distilling under reduced pressure

Sources & evidence

ORD record
ord-6f876f40763e4b7d92bfda9337b5d5e7
Source dataset
uspto-grants-1988_04
Patent number
US04737313

Reaction notes

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