Triphenyl phosphite → Butanal, 4-(acetyloxy)-2-methylene-

HRID 1703505Notes

Reaction equation

HRID 1703505 reaction equation
C([O:4][CH2:5][CH:6]=[CH:7][CH2:8][O:9][C:10](=[O:12])[CH3:11])(=O)C.[C:13]1(OP(OC2C=CC=CC=2)OC2C=CC=CC=2)C=CC=CC=1>[Rh].C1CCC=CCCC=1>[CH:5]([C:6]([CH2:7][CH2:8][O:9][C:10](=[O:12])[CH3:11])=[CH2:13])=[O:4]

Participants

4

Reactant 2

HCID 7540Triphenyl phosphiteHCID 1404022-Butene-1,4-diol diacetate

Product 1

HCID 11083989Butanal, 4-(acetyloxy)-2-methylene-Yield 50,545.699%

Reagents, catalysts & solvents 1

HCID 86627671HCID 86627671, compoundCatalyst

Procedure

A solution of 1,4-diacetoxy-2-butene (170 g.), (1,5-cyclooctadiene) rhodium (acetylacetonate) (0.17 g.) and triphenylphosphite (0.51 g.) was heated to 75° C. in a 1 liter stainless steel autoclave under a pressure of 2,000 psig of synthesis gas. After a few hours, the reaction was complete. After cooling and venting, the resulting solution was distilled to remove benzene. P-toluenesulphonic acid (0.5 g.) was added and the mixture was distilled (115°-120° C./5 mmHg). The resulting distillate was fractionated to give 2-formyl-4-acetoxybutene (118.1 g., 89% yield).

Workup

  1. waitAfter a few hours
  2. temperatureAfter cooling
  3. distillationthe resulting solution was distilled
  4. customto remove benzene
  5. additionP-toluenesulphonic acid (0.5 g.) was added
  6. distillationthe mixture was distilled (115°-120° C./5 mmHg)

Sources & evidence

ORD record
ord-94a5a4e6dbe64c90ae35163cc00251be
Source dataset
uspto-grants-1978_11
Patent number
US04124619

Reaction notes

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