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N,N-Dimethylaniline → (E)-4-carboxy-4'-[6-acryloyloxyhexyloxy]stilbene

HRID 970252
Notes
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Reaction equation

HRID 970252 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2].CN(C)C1C=CC=CC=1.[C:35](Cl)(=[O:38])[CH:36]=[CH2:37]>C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.O1CCOCC1>[C:1]([C:4]1[CH:5]=[CH:6][C:7](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:35](=[O:38])[CH:36]=[CH2:37])=[CH:14][CH:13]=2)=[CH:8][CH:9]=1)([OH:3])=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 13140Acryloyl chlorideHCID 59018740(E)-4-Carboxy-4'-[6-hydroxyhexyloxy]-stilbene

Product 1

HCID 59018738(E)-4-carboxy-4'-[6-acryloyloxyhexyloxy]stilbeneYield 71.3%

Reagents, catalysts & solvents 2

HCID 314042,6-Di-tert-butyl-4-methylphenolCatalyst
HCID 31275
1,4-Dioxane
Solvent
2×

Conditions

Temperature
60 °C

Procedure

A mixture of 4.38 g (12.8 mmole) of (E)-4-carboxy-4′-[6-hydroxyhexyloxy]stilbene (16), 1.87 g (15.4 mmole) of N,N-dimethylaniline, 1.38 g (15.4 mmole) of acryloyl chloride, 8 mg of 2,6-di-t-butyl-4-methylphenol and 9 ml of 1,4-dioxane was heated at 60° C. under a nitrogen atmosphere. After 3 hours the mixture was cooled and 10 ml of 1,4-dioxane were added. The product was collected on a filter and washed with 40 ml of ethanol. 3.6 g of product (71%) were obtained after drying over silica in a dessicator.

Workup

  1. temperatureAfter 3 hours the mixture was cooled
  2. customThe product was collected on
  3. filtrationa filter
  4. washwashed with 40 ml of ethanol

Sources & evidence

ORD record
ord-6ef9fbfaa89b4443ac35028ebc8d73ae
Source dataset
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07311948B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes