Thionyl Chloride → HCID 57968127, compound

HRID 1034535Notes

Reaction equation

HRID 1034535 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 (grams)) was dissolved in tetrahydrofurane (THF, 100 ml (milliliters)) at a room temperature, and a temperature of the resulting mixture was adjusted to a temperature of 0° C. (Celsius). Then, thionyl chloride (12 ml (milliliters), 1M in THF) was added to the mixture, and stirred for 30 minutes. Then, 4-(6-bromohexyloxy)phenol (2.5 g (grams)) and triethyl amine (13 ml (milliliters)) were added to the resulting reaction mixture, stirred at 0° C. (Celsius) for 1 hour, and then stirred at a room temperature overnight. Next day, a saturated ammonium chloride aqueous solution was poured into the reaction mixture, and the reaction was completed. The resulting reaction mixture was extracted three times with ethyl acetate (50 ml (milliliters)), and waster was removed over magnesium sulfate. Then, the solvents were evaporated, and the resulting reaction mixture was then purified using a column chromatography (developer solution: ethylacetate/hexane=1/2 volume ratio) to obtain 4-(6-bromo hexyloxy)phenyl 4-{[6-(acryloyloxy)hexyl]oxy}benzoate (5) (3 g (grams)).

Workup

  1. customwas adjusted to a temperature of 0° C. (Celsius)
  2. stirringstirred at 0° C. (Celsius) for 1 hour
  3. stirringstirred at a room temperature overnight
  4. customThe resulting reaction mixture
  5. extractionwas extracted three times with ethyl acetate (50 ml (milliliters)), and waster
  6. customwas removed over magnesium sulfate
  7. customThen, the solvents were evaporated
  8. customthe resulting reaction mixture
  9. customwas then purified

Sources & evidence

ORD record
ord-6443f120eee842b89ebc7183e3ed6996
Source dataset
uspto-grants-2013_10
Patent number
US08545717B2

Reaction notes

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