P-Xylene → 5-(Tetradecyloxy)-2-furoic acid

HRID 1111408Notes

Reaction equation

HRID 1111408 reaction equation
Br[C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:10]([OH:24])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[H-].[Na+].CC1C=CC(C)=CC=1>O.C(O)(=O)C>[CH2:10]([O:24][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][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 7809P-XyleneHCID 82091-TetradecanolHCID 24758Sodium hydrideHCID 685115-Bromo-2-furanecarboxylic acid

Product 1

HCID 1151755-(Tetradecyloxy)-2-furoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 57.2 (0.300 mole) of 5-bromo-2-furoic acid, 102.0 g (0.45 mole) of tetradecanol, 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-tetradecyloxy-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-9bc6a38a60a74b16a02c7fb17b8e5683
Source dataset
uspto-grants-1990_12
Patent number
US04980371

Reaction notes

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