Water → 4-{[4-(Dodecyloxy)benzoyl]oxy}benzoic acid

HRID 622064Notes

Reaction equation

HRID 622064 reaction equation
[CH2:1]([O:13][C:14]1[CH:30]=[CH:29][C:17]([C:18]([O:20][C:21]2[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=2)=[O:19])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[OH2:31]>C(O)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[CH2:1]([O:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([O:20][C:21]2[CH:28]=[CH:27][C:24]([C:25]([OH:31])=[O:26])=[CH:23][CH:22]=2)=[O:19])=[CH:29][CH:30]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 962WaterHCID 141726944-Formylphenyl 4-(dodecyloxy)benzoate

Product 1

HCID 158098334-{[4-(Dodecyloxy)benzoyl]oxy}benzoic acidYield 83%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent2×

Procedure

The 4-(4-n-dodecoxybenzoyloxy)-benzaldehyde produced in step A4 (17.4 g) was dissolved in acetic acid (60 ml) and treated with a solution of chromium trioxide (12.7 g) dissolved in 50% acetic acid added dropwise over 20 minutes at 40° C. After stirring at 45°-50° for 20 hours, water (150 ml) was added and the mixture stirred for 3 hours. The product separated and was recrystallised from acetic acid (55 ml) to give 4-(4-n-dodecoxybenzoyloxy)-benzoic acid (15 g, 83% theory).

Workup

  1. additionadded dropwise over 20 minutes at 40° C
  2. stirringthe mixture stirred for 3 hours
  3. customThe product separated
  4. customwas recrystallised from acetic acid (55 ml)

Sources & evidence

ORD record
ord-7929c27e086a4fafaa07b4208cee7cc7
Source dataset
uspto-grants-1988_09
Patent number
US04769176

Reaction notes

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