Benzene → p-(5-n-Butyl-1,3-dioxan-2-yl)phenyl p-n-butylbenzoate

HRID 2050139Notes

Reaction equation

HRID 2050139 reaction equation
[CH2:1]([CH:5]([CH2:8][OH:9])[CH2:6][OH:7])[CH2:2][CH2:3][CH3:4].[CH2:10]([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)=[CH:23][CH:22]=2)=[O:19])=[CH:16][CH:15]=1)[CH2:11][CH2:12][CH3:13].C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH2:10]([C:14]1[CH:30]=[CH:29][C:17]([C:18]([O:20][C:21]2[CH:22]=[CH:23][C:24]([CH:25]3[O:9][CH2:8][CH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6][O:7]3)=[CH:27][CH:28]=2)=[O:19])=[CH:16][CH:15]=1)[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 27952592-n-Butylpropane-1,3-diolHCID 5231030p-(4'-n-Butylbenzoyloxy)benzaldehyde

Product 1

HCID 15681131p-(5-n-Butyl-1,3-dioxan-2-yl)phenyl p-n-butylbenzoateYield 67.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-n-butylpropane-1,3-diol (6.6 g, 0.05 m) and p-(4'-n-butylbenzoyloxy)benzaldehyde (14.2 g, 0.05 m), benzene (100 ml) and a catalytic amount of 4-toluenesulfonic acid was azeotropically refluxed until no more water was collected. The solvent was evaporated and the residue was crystallized from ethanol to yield p-(5-n-butyl-1,3-dioxan-2-yl)phenyl p-n-butylbenzoate (13.4 g 67%) CN 79.2°-80.2° C., NL 160° C.

Workup

  1. customwas collected
  2. customThe solvent was evaporated
  3. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-a40763117d874804ba6751f7b4ae4843
Source dataset
uspto-grants-1980_04
Patent number
US04200580

Reaction notes

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