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

HRID 614762Notes

Reaction equation

HRID 614762 reaction equation
[CH2:1]([O:15][C:16]1[O: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+].COS(OC)(=O)=O.CO>CC(C)=O>[CH3:24][O:22][C:21]([C:19]1[O: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 1151755-(Tetradecyloxy)-2-furoic acid

Product 1

HCID 12361515Methyl 5-(tetradecyloxy)furan-2-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 10.0 g of (0.031 mole) of 5-tetradecyloxy-2-furoic acid, 200 ml of acetone and 4.3 g (0.031 mole) of potassium carbonate is stirred at room temperature after which 3.9 g (0.031 mole) of dimethylsulfate is added. The mixture is stirred with heating for about two and one-half 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 and recrystallized from methanol to give 5-tetradecyloxy-2-furoic acid methyl ester, M.P. 56°-58° C.

Workup

  1. additionis added
  2. additionis added
  3. filtrationfiltered
  4. customThe filtrate is evaporated to dryness
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-89f464e68182433fa42332d30cb643c6
Source dataset
uspto-grants-1979_03
Patent number
US04146623

Reaction notes

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