Water → HCID 131728043, compound

HRID 2384122Notes

Reaction equation

HRID 2384122 reaction equation
[C:1]([CH2:14][C:15]([CH2:18][C:19]([CH2:22][CH2:23]I)([F:21])[F:20])([F:17])[F:16])([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].CNC=[O:28].O>CCOCC>[C:1]([CH2:14][C:15]([CH2:18][C:19]([CH2:22][CH2:23][OH:28])([F:21])[F:20])([F:17])[F:16])([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2]

Participants

5

Reactant 3

HCID 962WaterHCID 31254N-MethylformamideHCID 1254825161,1,1,2,2,3,3,4,4,6,6,8,8-Tridecafluoro-10-iododecane

Product 1

HCID 131728043HCID 131728043, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

Then C4F9(CH2CF2)2CH2CH2I (10 g) and N-methylformamide (8.9 mL) were heated to 150° C. for 26 h. The reaction was cooled to 100° C., followed by the addition of water to separate the crude ester. Ethyl alcohol (3 mL) and p-toluene sulfonic acid (0.09 g) were added to the crude ester, and the reaction was stirred at 70° C. for 15 min. Then ethyl formate and ethyl alcohol were distilled out to give a crude product. The crude alcohol was dissolved in ether, washed with aqueous sodium sulfite, water, and brine in series, and dried over magnesium sulfate. The product was distilled to give C4F9(CH2CF2)2CH2CH2OH: bp 90˜94° C. at 2 mmHg Pascals).

Workup

  1. customto separate the crude ester
  2. additionEthyl alcohol (3 mL) and p-toluene sulfonic acid (0.09 g) were added to the crude ester
  3. distillationThen ethyl formate and ethyl alcohol were distilled out
  4. customto give a crude product
  5. washwashed with aqueous sodium sulfite, water, and brine in series
  6. dry with materialdried over magnesium sulfate
  7. distillationThe product was distilled

Sources & evidence

ORD record
ord-c9db64c14c0d499fa6c43b4ce53bd9e2
Source dataset
uspto-grants-2012_09
Patent number
US08263670B2

Reaction notes

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