Methanol → HCID 15001768, compound

HRID 1493723Notes

Reaction equation

HRID 1493723 reaction equation
[F-].[Na+].[CH3:3][OH:4].[F:5][C:6]1([C:20]([F:23])([F:22])[F:21])[O:11][C:10]([F:13])([F:12])[C:9](F)([C:14]([F:17])([F:16])[F:15])[O:8][C:7]1=[O:19].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[F:5][C:6]([C:20]([F:23])([F:22])[F:21])([O:11][C:10]([F:13])([F:12])[C:9](=[O:8])[C:14]([F:15])([F:17])[F:16])[C:7]([O:4][CH3:3])=[O:19]

Participants

5

Reactant 4

HCID 887MethanolHCID 5235Sodium FluorideHCID 14812Phosphorus oxide (P4O10)HCID 110958Perfluoro-3,6-dimethyl-1,4-dioxan-2-one

Product 1

HCID 15001768HCID 15001768, compoundYield 85%

Procedure

A suspension of 50.4 g (1.2 mol) of NaF in 128 g (4.0 mol) of methanol was stirred and cooled with an ice bath while 310 g (1.0 mol) of perfluoro(3,6-dimethyl-2-oxo-1,4-dioxane) was added at a rate sufficient to maintain a temperature of 25°-30° C. The ice bath was removed after completion of the addition and the reaction mixture was stirred overnight. The NaF.HF was filtered off, the filter cake was rinsed well with ether, and the filtrates were added to 213 g (1.5 mol) of P2O5. The resultant mixture was allowed to stand for about 65 h and then distilled to give 272.6 g (85%) of methyl perfluoro(2-methyl-5-oxo-3-oxahexanoate), bp 48°-51° (50 mm), identified by IR and NMR.

Workup

  1. additionwas added at a rate sufficient
  2. temperatureto maintain a temperature of 25°-30° C
  3. customThe ice bath was removed
  4. additionafter completion of the addition
  5. stirringthe reaction mixture was stirred overnight
  6. filtrationHF was filtered off
  7. washthe filter cake was rinsed well with ether
  8. distillationdistilled

Sources & evidence

ORD record
ord-0b1eb2a11a884c5790805cc0bc5d5283
Source dataset
uspto-grants-1991_06
Patent number
US05023362

Reaction notes

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