Methanol → Methyl 5-(tetradecyloxy)thiophene-2-carboxylate

HRID 328375Notes

Reaction equation

HRID 328375 reaction equation
[CH2:1]([O:15][C:16]1[S:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][CH:17]=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].[C:24](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.CO>CC(C)=O>[CH3:24][O:22][C:21]([C:19]1[S:20][C:16]([O:15][CH2:1][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])=[CH:17][CH:18]=1)=[O:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 123615105-(Tetradecyloxy)thiophene-2-carboxylic acid

Product 1

HCID 54242510Methyl 5-(tetradecyloxy)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 10.6 g of (0.031 mole) of 5-tetradecyloxy-2-thiophene carboxylic acid, 200 ml of acetone, and 4.3 g (0.031 mole) of potassium carbonate is stirred at room temparature after which 3.9 g (0.031 mole) of dimethyl sulfate is added. The mixture is stirred with heating for about 21/2 hours during which time 10 ml of methanol is added. The mixture is then diluted with 100 ml of acetone and filtered. The filtrate is evaporated to dryness to give 5-tetradecyloxy-2-thiophene carboxylic acid methyl ester.

Workup

  1. additionis added
  2. additionis added
  3. filtrationfiltered
  4. customThe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-f4d6a56efc5c4f25ba4d00fe3050ae53
Source dataset
uspto-grants-1977_04
Patent number
US04017514

Reaction notes

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