Sodium Nitrite → Perfluoro-2-[3-(methoxy)propoxy]acetic acid

HRID 2407649Notes

Reaction equation

HRID 2407649 reaction equation
N([O-])=O.[Na+].CC(O[Na])=[O:7].[F:10][C:11]([F:29])([O:14][C:15]([F:28])([F:27])[C:16]([F:26])([F:25])[C:17]([F:24])([F:23])[O:18][C:19]([F:22])([F:21])[F:20])[CH2:12][OH:13]>CC1(C)N([O])C(C)(C)CCC1.C(O)(=O)C>[F:10][C:11]([F:29])([O:14][C:15]([F:27])([F:28])[C:16]([F:25])([F:26])[C:17]([F:23])([F:24])[O:18][C:19]([F:20])([F:21])[F:22])[C:12]([OH:7])=[O:13]

Participants

6

Reactant 3

HCID 23668193Sodium NitriteHCID 66573360HCID 66573360, compoundHCID 178418247HCID 178418247, compound

Product 1

HCID 52915300Perfluoro-2-[3-(methoxy)propoxy]acetic acidYield 78%

Reagents, catalysts & solvents 2

HCID 2724126TempoCatalystHCID 176Acetic AcidSolvent

Procedure

70 mL of acetic acid, 0.24 g sodium nitrite, TEMPO (0.18 g), CH3CO2Na (3.69 g) and 5 g of 2,2-difluoro-2-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxy-propoxy)-ethanol were placed in the reaction vessel described in example 17. The reaction was carried out and worked up as described in example 9. Distillation of the residue gave 4.05 g of the acid (20 mmHg, 65° C.). Yield: 78%.

Workup

  1. distillationDistillation of the residue

Sources & evidence

ORD record
ord-03264322ca43497fa7022a4d02f0a3b3
Source dataset
uspto-grants-2014_08
Patent number
US08809580B2

Reaction notes

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