Potassium Carbonate → HCID 54194955, compound

HRID 1463020Notes

Reaction equation

HRID 1463020 reaction equation
[CH2:1]([CH:6]1[O:11][C:10]2[CH:12]=[CH:13][C:14]([CH:16]=O)=[CH:15][C:9]=2[CH2:8][O:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].O1CCO[CH2:26][CH2:25]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[CH2:1]([CH:6]1[O:11][C:10]2[CH:12]=[CH:13][C:14]([CH:16]=[CH:25][CH3:26])=[CH:15][C:9]=2[CH2:8][O:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 20450699HCID 20450699, compound

Product 1

HCID 54194955HCID 54194955, compound

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Procedure

A mixture of 4.8 g of 2-pentyl-1,3-benzodioxan-6-carboxaldehyde, 100 ml of dioxan, 5 g of finely powdered potassium carbonate and 11.5 g of ethyltriphenylphosphonium bromide is heated to boiling under reflux for 24 hours. The inorganic salts are filtered off and back-washed with dioxan and the filtrate is evaporated. The residue is stirred up with hexane. Insoluble triphenylphosphine oxide is filtered off and the filtrate is evaporated. The residue is distilled at 210° C./11 mmHg in a bulb-tube. The turbid distillate is re-distilled at 130° C./0.1 mmHg in a bulb-tube. 2.5 g of crude, oily 2-pentyl-6-propenyl-1,3-benzodioxan are obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 24 hours
  3. filtrationThe inorganic salts are filtered off
  4. washback-washed with dioxan
  5. customthe filtrate is evaporated
  6. filtrationInsoluble triphenylphosphine oxide is filtered off
  7. customthe filtrate is evaporated
  8. distillationThe residue is distilled at 210° C./11 mmHg in a bulb-tube
  9. distillationThe turbid distillate is re-distilled at 130° C./0.1 mmHg in a bulb-tube

Sources & evidence

ORD record
ord-5fcbddff6ab84c49b6f89bd2793a5139
Source dataset
uspto-grants-1984_07
Patent number
US04462923

Reaction notes

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