Acetone → HCID 86591073, compound

HRID 1783278Notes

Reaction equation

HRID 1783278 reaction equation
O[C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]=[N:33][C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=2)=[CH:28][CH:27]=1.CC(C)=[O:43]>O>[CH3:40][C:37]1[CH:38]=[CH:39][C:34]([N:33]=[N:32][C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:43][C:5]3[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:3][CH:2]=[CH:12][C:6]=3[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:27][CH:28]=2)=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 606456Diethyl 5-hydroxyisophthalateHCID 11188003HCID 11188003, compound

Product 1

HCID 86591073HCID 86591073, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 l three-neck flask was charged with 16.6 g (0.07 mol) of diethyl 5-hydroxyisophthalate, 26.1 g (0.07 mol) of 4-(6-bromohexyloxy)-4′-methylazobenzene and 15.1 g (0.11 mol) of potassium carbonate anhydride. To the mixture was added 300 ml of acetone and the system was refluxed under heating to react for 24 hours. After the reaction was completed, the system was poured into 1500 ml of cool water to obtain diethyl {6-[4-(4-methylphenylazo)phenoxy]hexyloxy}isophthalate, which was then separated by filtration and dried under reduced pressure (yield: 83% (35.1 g)). The product was recrystallized from acetone twice to obtain 30.1 g (80.1%) of a target product, diethyl (5-{6-[4-(4-methylphenylazo)phenoxy]hexyloxy}isophthalate. It was found from an analysis using high performance liquid chromatography that the purity of the product was 98.5% or more. The resulting compound was subjected to measurements of infrared absorption spectrum (IR) and nuclear magnetic resonance (NMR). The results are shown in the following.

Workup

  1. temperaturethe system was refluxed
  2. temperatureunder heating
  3. customto react for 24 hours

Sources & evidence

ORD record
ord-8735bffa835f4857a0342a600b807818
Source dataset
uspto-grants-2009_03
Patent number
US07501210B2

Reaction notes

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