Water → 5-(3,7,11,15-Tetramethylhexadecyloxy)-2-furoic acid

HRID 596633

Reaction equation

HRID 596633 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:21])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:25]1[O:29][C:28]([C:30]([OH:32])=[O:31])=[CH:27][CH:26]=1.O>C1(C)C=CC=CC=1>[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:21])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:3][CH2:4][O:5][C:25]1[O:29][C:28]([C:30]([OH:32])=[O:31])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 102459DihydrophytolHCID 2348535-Chlorofuran-2-carboxylic acid

Product 1

HCID 214504315-(3,7,11,15-Tetramethylhexadecyloxy)-2-furoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 59.8 g (0.2 mole) of 3,7,11,15-tetramethyl-1-hexadecanol and 19.2 g (0.4 mole) of sodium hydride (50% in oil) in 1 liter of toluene is refluxed with stirring for 2 hours then cooled to room temperature. To the mixture 29.3 g (0.2 mole) of 5-chloro-2-furoic acid is added and the mixture is refluxed with stirring for 24 hours. Upon cooling to room temperature the mixture is acidified with glacialacetic acid and water is added. The toluene layer is evaporated and allowed to crystallize to give 5-(3,7,11,15-tetramethylhexadecyloxy)-2-furoic acid.

Workup

  1. temperatureis refluxed
  2. temperaturethe mixture is refluxed
  3. stirringwith stirring for 24 hours
  4. temperatureUpon cooling to room temperature the mixture
  5. additionis added
  6. customThe toluene layer is evaporated
  7. customto crystallize

Sources & evidence

ORD record
ord-fd13263df78048ae968f86bbe42ce2d6
Source dataset
uspto-grants-1977_03
Patent number
US04011334

Linked notes

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