Propionic Acid → HCID 23454177, compound

HRID 1277515Notes

Reaction equation

HRID 1277515 reaction equation
[C:1]([C:20]1[CH:26]=[C:25]([OH:27])[CH:24]=[CH:23][C:21]=1[OH:22])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:28](O)(=[O:31])[CH2:29][CH3:30].S(=O)(=O)(O)O>>[CH2:1]([C:20]1[CH:26]=[C:25]([O:27][C:28](=[O:31])[CH2:29][CH3:30])[CH:24]=[CH:23][C:21]=1[OH:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 1118Sulfuric AcidHCID 12516039HCID 12516039, compound

Product 1

HCID 23454177HCID 23454177, compoundYield 39.8%

Conditions

Temperature
140 °C

Procedure

To 5.2 g of n-octadecanoylhydroquinone and 6.0 g of anhydrous propionic acid were added 1.5 ml of concentrated sulfuric acid and thereafter the mixture was heated on an oil bath at 140° C. for 15 minutes. After being allowed to be cooled, the mixture was added to ice and extracted with ethyl acetate. The extract was washed with water and dried. Purification through silica gel column chromatography [developing solvent: benzene/acetone (9:1)] gave 2.3 g of the end product having m.p. 75°-78° C. Elemental analysis:

Workup

  1. temperatureto be cooled
  2. additionthe mixture was added to ice
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customPurification through silica gel column chromatography [developing solvent: benzene/acetone (9:1)]

Sources & evidence

ORD record
ord-35ef3c00c8fc42298ee96830b7d39642
Source dataset
uspto-grants-1981_07
Patent number
US04277553

Reaction notes

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