P-Xylene → HCID 70416722, compound

HRID 746071Notes

Reaction equation

HRID 746071 reaction equation
Br[C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:10]([OH:25])[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][CH3:24].[H-].[Na+].CC1C=CC(C)=CC=1>O.C(O)(=O)C>[CH2:10]([O:25][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][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][CH3:24]

Participants

7

Reactant 4

HCID 7809P-XyleneHCID 24758Sodium hydrideHCID 685115-Bromo-2-furanecarboxylic acidHCID 5364682HCID 5364682, compound

Product 1

HCID 70416722HCID 70416722, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 57.2 (0.300 mole) of 5-bromo-2-furoic acid, 121.0 g (0.45 mole) of cis-9-pentadecenol, 18.0 g (0.750 mole) of sodium hydride and 2 liters of p-xylene are heated to reflux 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 recrystallized from hexane to give 5-(cis-9-pentadecenyloxy)-2-furoic acid.

Workup

  1. temperatureare heated
  2. temperatureto reflux for 48 hours
  3. temperatureto cool
  4. customThe organic layer is separated
  5. customdried
  6. customevaporated to dryness
  7. customthe residue recrystallized from hexane

Sources & evidence

ORD record
ord-aa8e9c2421ac4708a2d23b5ff9f2fc36
Source dataset
uspto-grants-1986_07
Patent number
US04602099

Reaction notes

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