Methanol → HCID 86732646, compound

HRID 523321Notes

Reaction equation

HRID 523321 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[OH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27](/[CH:30]=[CH:31]/[C:32]([O-:34])=[O:33])=[CH:26][C:25]=1[O:35][CH3:36].N1C=CC=C[CH:38]=1.CO>C1(C)C=CC=CC=1.CN(C=O)C.CN(C)C1C=CN=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27](/[CH:30]=[CH:31]/[C:32]([O:34][CH3:38])=[O:33])=[CH:26][C:25]=1[O:35][CH3:36])=[O:8])([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 74323,5-Dinitrobenzoyl chlorideHCID 21841413HCID 21841413, compound

Product 1

HCID 86732646HCID 86732646, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

17.9 g (78 mmol) of 3,5-dinitrobenzoyl chloride are dissolved in 147 mL of toluene and 20 drops of DMF were incorporated. 24 g (78 mmol) of (2E)-3-{4-[(6-hydroxyhexyl)oxy]-3-methoxyphenyl}prop-2-enoate, 0.475 g (4 mmol) of 4-dimethylaminopyridine and 9.23 g (117 mmol) of pyridine are added. The mixture is stirred at room temperature for 96 hours. The solution is then heated up to 60° C. and 58 ml of MeOH are added. The suspension is stirred at room temperature for 1 hour and at 0° C. for 1 hour. The precipitate is filtered off. Chromatography of the residue using toluene: ethyl acetate 19:1 following by toluene: ethyl acetate 9:1 yielded 25 g (64%) of pure 6-{2-methoxy-4-[(1E)-3-methoxy-3-oxoprop-1-enyl]phenoxy}hexyl 3,5-dinitrobenzoate as an orange powder.

Workup

  1. temperatureThe solution is then heated up to 60° C.
  2. stirringThe suspension is stirred at room temperature for 1 hour and at 0° C. for 1 hour
  3. filtrationThe precipitate is filtered off

Sources & evidence

ORD record
ord-8cf8e098017c461788190104f7206eb1
Source dataset
uspto-grants-2016_05
Patent number
US09334366B2

Reaction notes

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