Water → HCID 13393463, compound

HRID 615488Notes

Reaction equation

HRID 615488 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].OC1C=CC([C:17](=[O:35])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=CC=1C(O)=O.[OH2:36].C1(C)C=CC(S([O:46][CH3:47])(=O)=O)=CC=1.[C:49]1(C)[C:50]([CH3:55])=[CH:51][CH:52]=[CH:53][CH:54]=1>>[CH3:47][O:46][C:49]1[CH:54]=[CH:53][C:52]([C:17](=[O:35])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:51][C:50]=1[C:55]([O:4][CH3:1])=[O:36]

Participants

6

Reactant 5

HCID 962WaterHCID 6645Methyl p-toluenesulfonateHCID 7237O-XyleneHCID 11430Potassium CarbonateHCID 51009112-Hydroxy-5-(1-oxooctadecyl)benzoic acid

Product 1

HCID 13393463HCID 13393463, compound

Procedure

Potassium carbonate (11.4 mmole) was added to a solution of the product of Example 4 (5.7 mmole) in 50 ml xylene, heated to reflux, and the water formed removed with a Dean-Stark trap. After 1 hour the Dean-Stark trap was drained. The solution was cooled to room temperature and methyl p-toluenesulfonate (17.1 mmole) added. The solution was heated to 70° C. for 20 hours, and refluxed for one hour to remove the water formed. After the white solid was filtered and discarded, the filtrate was concentrated under vacuum to a solid, which was was recrystallized from hot hexane, to give the title compound (1.6 g), m.p. ca. 73°-74° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customremoved with a Dean-Stark trap
  4. temperatureThe solution was heated to 70° C. for 20 hours
  5. temperaturerefluxed for one hour
  6. customto remove the water
  7. customformed
  8. filtrationAfter the white solid was filtered
  9. concentrationthe filtrate was concentrated under vacuum to a solid, which
  10. customwas was recrystallized from hot hexane

Sources & evidence

ORD record
ord-eab53c796c03492aa1954ad04b104d06
Source dataset
uspto-grants-1985_02
Patent number
US04499295

Reaction notes

Loading…