Carbon Dioxide → 5-[(3,7,11,15-Tetramethylhexadecyl)oxy]thiophene-2-carboxylic acid

HRID 596659Notes

Reaction equation

HRID 596659 reaction equation
[CH3:1][CH:2]([CH2:11][CH2:12][CH2:13][CH:14]([CH3:26])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:3][CH2:4][O:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.[C:27](=[O:29])=[O:28].C(O)C.O>CCOCC.[Na].[Hg]>[CH3:1][CH:2]([CH2:11][CH2:12][CH2:13][CH:14]([CH3:26])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:3][CH2:4][O:5][C:6]1[S:7][C:8]([C:27]([OH:29])=[O:28])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 702EthanolHCID 962WaterHCID 214418222-[(3,7,11,15-Tetramethylhexadecyl)oxy]thiophene

Product 1

HCID 214418155-[(3,7,11,15-Tetramethylhexadecyl)oxy]thiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

When in Example 3, 1-bromo-3,7,11,15-tetramethylhexadecane is substituted for 1-bromohexadecane, 2-(3,7,11,15-tetramethylhexadecyloxy)thiophene is obtained. A solution of 38.1 g (0.1 mole) of 2-(3,7,11,15-tetramethylhexadecyloxy)-thiophene in 50 ml of anhydrous ether is added over a 4 hour period to 6.0 g of sodium amalgam in 100 ml of hydrous ether at reflux temperature (36°-39° C) under slight nitrogen pressure. The mixture is refluxed an additional 2 hours, then cooled to room temperature and carbonated by adding freshly crushed dry ice after which 20 ml of ethanol is added dropwise followed by the addition of 50 ml of water. The aqueous solution is separated from the ether layer, filtered and acidified with hydrochloric acid to precipitate 5-(3,7,11,15-tetramethylhexadecyloxy)-2-thiophenecarboxylic acid.

Workup

  1. temperatureat reflux temperature (36°-39° C) under slight nitrogen pressure
  2. temperatureThe mixture is refluxed an additional 2 hours
  3. additionis added dropwise
  4. customThe aqueous solution is separated from the ether layer
  5. filtrationfiltered
  6. customto precipitate 5-(3,7,11,15-tetramethylhexadecyloxy)-2-thiophenecarboxylic acid

Sources & evidence

ORD record
ord-efcf802ecf4c4103a9c5a40594377451
Source dataset
uspto-grants-1977_03
Patent number
US04011333

Reaction notes

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