4-Hydroxybenzaldehyde → p-Octyloxycarbonyloxybenzaldehyde

HRID 648874

Reaction equation

HRID 648874 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].C1(C)C=CC=CC=1.Cl>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 313Hydrochloric AcidHCID 1140TolueneHCID 81956Carbonochloridic acid, octyl ester

Product 1

HCID 13828007p-OctyloxycarbonyloxybenzaldehydeYield 65.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Commercially available p-hydroxybenzaldehyde (50 g) was dissolved in pyridine (400 ml), followed by dropwise adding octyl chloroformate (85 g) under ice cooling, heating on a water bath, allowing the reaction mixture to stand overnight, adding toluene (300 ml) and 6N hydrochloric acid, separating the liquid layer, further washing with an aqueous solution of 2N NaOH, washing with water, drying and distilling off toluene to obtain a raw product of p-octyloxycarbonyloxybenzaldehyde (75 g).

Workup

  1. temperatureheating on a water bath
  2. customseparating the liquid layer
  3. washfurther washing with an aqueous solution of 2N NaOH
  4. washwashing with water
  5. customdrying
  6. distillationdistilling off toluene

Sources & evidence

ORD record
ord-2540e33eaeda41cbb2db7992398f7311
Source dataset
uspto-grants-1988_04
Patent number
US04737313

Linked notes

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