Hydrochloric Acid → HCID 21482459, compound

HRID 1415490Notes

Reaction equation

HRID 1415490 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:60])([F:59])[C:12]([F:58])([F:57])[O:13][C:14]([F:56])([F:55])[C:15]([F:54])([C:50]([F:53])([F:52])[F:51])[O:16][C:17]([F:49])([F:48])[C:18]([F:47])([F:46])[O:19][C:20]([F:45])([C:41]([F:44])([F:43])[F:42])[C:21]([F:40])([F:39])[O:22][C:23]([F:38])([F:37])[C:24]([F:36])([F:35])[C:25]2[CH:30]=[CH:29][C:28]([O:31]C(=O)C)=[CH:27][CH:26]=2)=[CH:7][CH:6]=1)(=O)C.Cl.O>CO>[OH:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]([F:35])([F:36])[C:23]([F:37])([F:38])[O:22][C:21]([F:39])([F:40])[C:20]([F:45])([C:41]([F:42])([F:43])[F:44])[O:19][C:18]([F:46])([F:47])[C:17]([F:48])([F:49])[O:16][C:15]([F:54])([C:50]([F:51])([F:52])[F:53])[C:14]([F:55])([F:56])[O:13][C:12]([F:58])([F:57])[C:11]([F:60])([F:59])[C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 53905101HCID 53905101, compound

Product 1

HCID 21482459HCID 21482459, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-iodophenyl acetate (7.86 g, 0.030 mole) and 1,14-diiodoerfluoro-5,10-dimethyl-3,6,9,12-tetraoxatetradecane (9.20 g, 0.010 mole) in 45 ml of N,N-dimethylformamide was added copper bronze (5.08 g, 0.080 g atom). This slurry was stirred under nitrogen at 115°-117° C for 96 hours. The cooled reaction mixture was added to a stirred mixture of 150 ml of ether and 200 ml of water. The cuprous salts and excess copper were filtered off and the ether layer was washed repeatedly with water until free from the reaction solvent. The ethereal solution was evaporated to dryness to give a brown oil which was refluxed in 20 ml of acetic anhydride for 15 minutes. The excess acetic anhydride was distilled off and the residue was distilled under reduced pressure to give 3.40 g of 1,14-bis (4-acetoxyphenyl)perfluoro-5,10-dimethyl-3,6,9,12-tetraoxatetradecane, b.p. 180°-185° C/0.30 mm. This water-white oil was refluxed for an hour in a solution of 10 ml of concentrated hydrochloric acid (0.12 mole) in 100 ml of methanol. The solvent was evaporated under reduced pressure and the resultant tan residue was taken up in 600 ml of hexane. This solution was treated with charcoal, filtered, and reduced in volume to give 2.72 g (32% yield) of product (III) as a viscous water-white oil.

Workup

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

Sources & evidence

ORD record
ord-73a190fb0106413eaed3da8613ca52aa
Source dataset
uspto-grants-1977_01
Patent number
US04005142

Reaction notes

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