O-Xylene → 5-(Tetradecyloxy)thiophene-2-carboxylic acid

HRID 596652Notes

Reaction equation

HRID 596652 reaction equation
[CH2:1]([OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[H-].[Na+].C1(C)C(C)=CC=CC=1.Cl[C:27]1[S:31][C:30]([C:32]([OH:34])=[O:33])=[CH:29][CH:28]=1>C(O)(=O)C>[CH2:1]([O:15][C:27]1[S:31][C:30]([C:32]([OH:34])=[O:33])=[CH:29][CH:28]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 82091-TetradecanolHCID 24758Sodium hydrideHCID 950485-Chloro-2-thiophenecarboxylic acid

Product 1

HCID 123615105-(Tetradecyloxy)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 21.4 g (0.100 mole) of 1-tetradecanol, 5.9 g (0.146 mole) of sodium hydride (59.5% in oil) and 300 ml of dried xylene is heated to reflux with stirring for 2 hours then allowed to cool after which 7.5 g (0.046 mole) of 5-chloro-2-thiophenecarboxylic acid is added. The mixture is refluxed for 64 hours after which the mixture is cooled and poured into a water-ice mixture, acidified with acetic acid, and extracted with the addition of ether. The ether is evaporated and aqueous layer extracted 5 times with water: strong ammonia solution (1:1). The combined aqueous extract is acidified with acetic acid. The solid obtained is crystallized twice from hexane to give 5-(tetradecyloxy)-2-thiophenecarboxylic acid, M.P. 95°-96° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. additionis added
  4. temperatureThe mixture is refluxed for 64 hours after which the mixture
  5. temperatureis cooled
  6. extractionextracted with the addition of ether
  7. customThe ether is evaporated
  8. extractionaqueous layer extracted 5 times with water
  9. extractionThe combined aqueous extract
  10. customThe solid obtained
  11. customis crystallized twice from hexane

Sources & evidence

ORD record
ord-a1668ae788b04b2da1a1758dd518688f
Source dataset
uspto-grants-1977_03
Patent number
US04011333

Reaction notes

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