Acetic Acid → HCID 68122754, compound

HRID 438018Notes

Reaction equation

HRID 438018 reaction equation
[CH2:1](O)[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:37])C>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([O:37][C:30]1([C:32]([OH:34])=[O:33])[CH2:29][CH:28]=[CH:27][S:31]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 7237O-XyleneHCID 82091-TetradecanolHCID 24758Sodium hydrideHCID 950485-Chloro-2-thiophenecarboxylic acid

Product 1

HCID 68122754HCID 68122754, compound

Procedure

A mixture of 214 g (1.0 mole) of 1-tetradecanol, 59 g (1.46 mole) of sodium hydride (59.5% in oil) and 3 l. of dried xylene is heated to reflux with stirring for two hours, then allowed to cool after which 75 g (0.46 mole) of 5-chloro-2-thiophene carboxylic acid is added. The mixture is refluxed for 64 hours after which it is cooled and poured into a waterice mixture, acidified with acetic acid and extracted with the addition of ether. The ether is evaporated, and the xylene layer extracted five 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 2-(5-tetradecyloxy)thiophene carboxylic acid, M.P. 95°-96° C.

Workup

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

Sources & evidence

ORD record
ord-6f5f1805fa084420af9e35042cf05b81
Source dataset
uspto-grants-1977_06
Patent number
US04032647

Reaction notes

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