Ethanol → HCID 56637922, compound

HRID 1903322Notes

Reaction equation

HRID 1903322 reaction equation
[CH2:1]([OH:3])[CH3:2].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:8][CH:7]=1.C(OCC)(OCC)O[CH2:18][CH3:19].C(=O)(O)[O-]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>[CH2:1]([O:3][C:12]([O:15][CH2:18][CH3:19])([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH3:4])=[CH:7][CH:8]=1)[CH2:13][CH3:14])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 769Bicarbonate IonHCID 31214Ethyl orthoformateHCID 671444-Propanoylanisole

Product 1

HCID 56637922HCID 56637922, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8471TriethylamineSolvent

Procedure

40 ml of absolute ethanol and 0.75 g of p-toluenesulphonic acid are placed in a round flask which is fitted with a stirrer, thermometer, condenser and dropping funnel. Now, there are added dropwise within 15 minutes while stirring 120 g of p-methoxy-propiophenone and subsequently within 1 hour 108 g of triethyl orthoformate. The temperature is held below 3° C. The mixture is subsequently stirred for a further 22 hours at room temperature. The mixture is adjusted to pH 8 with 3.6 g of triethylamine and then poured into 40 ml of 5% bicarbonate solution and 60 g of ice. The aqueous phase is separated and extracted with ether. The combined organic phases are washed with 5% bicarbonate solution and, after the addition of 0.2 g of sodium carbonate, the solvent is removed by evaporation under a vacuum and the residue is distilled over a 15 cm column. There are obtained 36.7 g of p-methoxy-propiophenone diethyl ketal (yield: 21% of theory). B.p.= 83°-84° C./0.4 mmHg; nD20 =1.4858; d420 =0.9988.

Workup

  1. customwhich is fitted with a stirrer
  2. customthermometer, condenser and dropping
  3. additionNow, there are added dropwise within 15 minutes
  4. customis held below 3° C
  5. customThe aqueous phase is separated
  6. extractionextracted with ether
  7. washThe combined organic phases are washed with 5% bicarbonate solution
  8. additionafter the addition of 0.2 g of sodium carbonate
  9. customthe solvent is removed by evaporation under a vacuum
  10. distillationthe residue is distilled over a 15 cm column

Sources & evidence

ORD record
ord-2fc3ed016dc940b09d8ea0b44c855b42
Source dataset
uspto-grants-1984_03
Patent number
US04435585

Reaction notes

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