Acetic Anhydride → HCID 21482467, compound

HRID 1415491Notes

Reaction equation

HRID 1415491 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].I[C:13]([F:56])([F:55])[C:14]([F:54])([F:53])[O:15][C:16]([F:52])([F:51])[C:17]([F:50])([F:49])[O:18][C:19]([F:48])([F:47])[C:20]([F:46])([F:45])[O:21][C:22]([F:44])([F:43])[C:23]([F:42])([F:41])[C:24]([F:40])([F:39])[C:25]([F:38])([F:37])[C:26]([F:36])([F:35])[O:27][C:28]([F:34])([F:33])[C:29]([F:32])([F:31])I.[C:57]([O:60][C:61](=O)[CH3:62])(=[O:59])[CH3:58]>[Cu].CCOCC>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:13]([F:56])([F:55])[C:14]([F:54])([F:53])[O:15][C:16]([F:52])([F:51])[C:17]([F:50])([F:49])[O:18][C:19]([F:48])([F:47])[C:20]([F:46])([F:45])[O:21][C:22]([F:44])([F:43])[C:23]([F:42])([F:41])[C:24]([F:40])([F:39])[C:25]([F:38])([F:37])[C:26]([F:36])([F:35])[O:27][C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[C:5]2[CH:10]=[CH:62][C:61]([O:60][C:57](=[O:59])[CH3:58])=[CH:7][CH:6]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 1417934-IodophenylacetateHCID 21482462HCID 21482462, compound

Product 1

HCID 21482467HCID 21482467, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 3283Diethyl EtherSolvent

Procedure

4-Iodophenyl acetate (7.86 g, 0.030 mole), 1,17-diiodoperfluoro-3,6,9,15-tetraoxaheptadecane (9.68 g, 0.010 mole), and copper bronze (5.08 g, 0.080 g atom) were stirred together under nitrogen at 113°-117° C for 48 hours. The cooled reaction mixture was added to 200 ml of ether. The cuprous salts and excess copper were filtered off and washed on the frit with ether. The ethereal solution was washed several times with water to remove the reaction solvent, dried over anhydrous magnesium sulfate, and reduced in volume under reduced pressure to yield a brown oil. The oil was refluxed with 10 ml of acetic anhydride for 20 minutes and the excess acetic anhydride then distilled off under reduced pressure. Distillation of the residue yielded 4.53 g of 1,17-bis (4-acetoxyphenyl)perfluoro-3,6,9,15-tetraoxaheptadecane, b.p. 184°-189° C/0.10 mm.

Workup

  1. customThe cooled reaction mixture
  2. filtrationThe cuprous salts and excess copper were filtered off
  3. washwashed on the frit with ether
  4. washThe ethereal solution was washed several times with water
  5. customto remove the reaction solvent
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customto yield a brown oil
  8. distillationthe excess acetic anhydride then distilled off under reduced pressure
  9. distillationDistillation of the residue

Sources & evidence

ORD record
ord-bdd62e93df7b479dbac9ab206d8e7dcf
Source dataset
uspto-grants-1977_01
Patent number
US04005142

Reaction notes

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