Phosphorus oxide (P4O10) → HCID 13911586, compound

HRID 653452Notes

Reaction equation

HRID 653452 reaction equation
[CH3:1][C:2]([CH3:13])([CH2:6][S:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:3]([OH:5])=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C=CC=CC=1>[CH3:13][C:2]1([CH3:1])[CH2:6][S:7][C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:3]1=[O:5]

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)2×HCID 13911646HCID 13911646, compound

Product 1

HCID 13911586HCID 13911586, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,2-dimethyl-3-(2-thienylthio)propanoic acid (53.65 g, 0.25 m), diatomaceous earth (54 g) and phosphorus pentoxide (87 g) in toluene (870 ml) was vigorously stirred and heated at 100° C. After 2 hours, additional phosphorous pentoxide (87 g) was added and the mixture was heated for 3 hours more. After filtering the hot mixture, the solid was washed with hot toluene (3×500 ml) and the combined filtrate and washings were concentrated under reduced pressure to afford 33.17 g (67%) of crude product. This material was combined with 2.89 g of crude product from a previous reaction and distilled to yield 25.07 g (46%) of pure product boiling at 96°-100° C./0.4 mm Hg.

Workup

  1. temperaturethe mixture was heated for 3 hours more
  2. filtrationAfter filtering the hot mixture
  3. washthe solid was washed with hot toluene (3×500 ml)
  4. concentrationthe combined filtrate and washings were concentrated under reduced pressure
  5. customto afford 33.17 g (67%) of crude product
  6. distillationdistilled

Sources & evidence

ORD record
ord-942fdea8a2494627b2a13917420b5a00
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

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