Thionyl Chloride → HCID 57968127, compound

HRID 1257941Notes

Reaction equation

HRID 1257941 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)(=[O:4])[CH:2]=[CH2:3].S(Cl)(Cl)=O.[Br:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37](O)=[CH:36][CH:35]=1.[Cl-].[NH4+]>O1CCCC1.C(N(CC)CC)C>[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][C:37]2[CH:38]=[CH:39][C:34]([O:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][Br:26])=[CH:35][CH:36]=2)=[O:18])=[CH:20][CH:21]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 25517Ammonium ChlorideHCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acidHCID 19894591HCID 19894591, compound

Product 1

HCID 57968127HCID 57968127, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

4-{[6-(acryloyloxy)hexyl]oxy}benzoic acid (4) (2.8 g) was dissolved in tetrahydrofuran (THF) (100 ml) at room temperature, and the resulting mixture was then adjusted to 0° C. Then, thionyl chloride (12 ml, 1M in THF) was added to the mixture, and the resulting mixture solution was stirred for 30 minutes. Subsequently, 4-(6-bromohexyloxy)phenol (2.5 g) and triethylamine (13 ml) were added to the mixture solution, and the resulting mixture is stirred at 0° C. for one hour, and then stirred at room temperature overnight. Then, an aqueous saturated ammonium chloride solution was poured into the reaction mixture to stop the reaction. The reaction product was extracted three times with ethyl acetate (50 ml) (50 ml×3). After removing water with magnesium sulfate and evaporating the solvent, the reaction product was refined by column chromatography (eluent: ethyl acetate/hexane=1/2) to obtain 4-(6-bromo hexyloxy)phenyl 4-{[6-(acryloyloxy)hexyl]oxy}benzoate (5) (3 g).

Workup

  1. customwas then adjusted to 0° C
  2. stirringthe resulting mixture is stirred at 0° C. for one hour
  3. stirringstirred at room temperature overnight
  4. customthe reaction
  5. extractionThe reaction product was extracted three times with ethyl acetate (50 ml) (50 ml×3)
  6. customAfter removing water with magnesium sulfate
  7. customevaporating the solvent

Sources & evidence

ORD record
ord-e196b9a8099240c8aa407390ff52e714
Source dataset
uspto-grants-2013_06
Patent number
US08465671B2

Reaction notes

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