P-Xylene → HCID 68142811, compound

HRID 1974170Notes

Reaction equation

HRID 1974170 reaction equation
Br[C:2]1[O:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[CH:3]=1.[CH2:10]([OH:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[H-].[Na+].CC1C=CC(C)=CC=1>O.C(O)(=O)C>[CH2:10]([O:28][C:2]1[O:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[CH:3]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 4

HCID 7809P-XyleneHCID 24758Sodium hydrideHCID 5284499Oleyl AlcoholHCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 68142811HCID 68142811, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 57.2 g (0.300 mole) of 5-bromo-3-furoic acid, 121.0 g (0.45 mole) of cis-9-octadecenol, 18.0 g (0.750 mole) of sodium hydride and 2 liters of p-xylene are heated to reflux with stirring for 48 hours. The mixture is allowed to cool, then is acidified with acetic acid, and diluted with 2 liters of water. The organic layer is separated, dried, evaporated to dryness, and the residue is recrystallized from hexane to give 5-(cis-9-octadecen-1-yloxy)-3-furoic acid.

Workup

  1. temperatureare heated
  2. temperatureto reflux
  3. temperatureto cool
  4. customThe organic layer is separated
  5. customdried
  6. customevaporated to dryness
  7. customthe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-341f87ad66354fbcaa9fe25aa95de2ee
Source dataset
uspto-grants-1976_12
Patent number
US04000164

Reaction notes

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