Hydrochloric Acid → HCID 22770278, compound

HRID 1764084Notes

Reaction equation

HRID 1764084 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:40])([F:39])[C:12]([F:38])([F:37])[O:13][C:14]([F:36])([F:35])[C:15]([F:34])([F:33])[O:16][C:17]([F:32])([F:31])[C:18]([F:30])([F:29])[C:19]2[CH:24]=[CH:23][C:22]([O:25]C(=O)C)=[CH:21][CH:20]=2)=[CH:7][CH:6]=1)(=O)C.Cl>CO>[OH:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([F:29])([F:30])[C:17]([F:31])([F:32])[O:16][C:15]([F:33])([F:34])[C:14]([F:35])([F:36])[O:13][C:12]([F:37])([F:38])[C:11]([F:40])([F:39])[C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22770279HCID 22770279, compound

Product 1

HCID 22770278HCID 22770278, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-iodophenyl acetate (26.8 g, 0.102 mole) and 1,8-dioodoperfluoro-3,6-dioxaoctane (20.0 g, 0.034 mole) in 125 ml of N,N-dimethylformamide was added copper bronze (17.3 g, 0.273 g atom). This slurry was stirred under nitrogen at 105°-110° C for 96 hours. The cooled reaction mixture was added to a stirred mixture of 200 ml of ether and 300 ml of water. The cuprous salts and excess copper were filtered off and washed with ether on the frit. The ether layer was then washed repeatedly with water until free from the reaction solvent. The ethereal solution was evaporated to dryness to give 23 g of brown oil which was refluxed in 20 ml of acetic anhydride for 40 minutes. The excess acetic anhydride was distilled off and the residue was distilled under reduced pressure to give 13.5 g of 1,8-bis(4-acetoxyphenyl)perfluoro-3,6-dioxaoctane, bp 158°-161° C/0.005 mm. This water-white oil was refluxed for 40 minutes in a solution of 22 ml of concentrated hydrochloric acid in 225 ml of methanol. The solvent was evaporated under reduced pressure and the resultant tan residue was taken up in a liter of hexane. This solution was treated with charcoal, filtered, and cooled to give 8.20 g (46% yield) of light pink crystals, mp 118°-120° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionThis solution was treated with charcoal
  3. filtrationfiltered
  4. temperaturecooled

Sources & evidence

ORD record
ord-9ed4384a3b374ffebe5cd98f4ed9ba97
Source dataset
uspto-grants-1978_09
Patent number
US04115367

Reaction notes

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