Benzyl Alcohol → 2-[5-(Tetradecyloxy)-2-furoyl]acetic acid benzyl ester

HRID 1974175Notes

Reaction equation

HRID 1974175 reaction equation
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([CH2:23][C:24]([OH:26])=[O:25])=[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(=O)=O.[CH2:30](O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[CH2:30]([O:25][C:24](=[O:26])[CH2:23][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:22])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 280Carbon DioxideHCID 214887552-[5-(Tetradecyloxy)-2-furoyl]acetic acid

Product 1

HCID 539183582-[5-(Tetradecyloxy)-2-furoyl]acetic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10.0 g (0.027 mole) of 2-[5-(tetradecyloxy)-2-furoyl]acetic acid, 4.4 g (0.027 mole) of N,N'-carbonyldiimidazole, and anhydrous tetrahydrofuran is stirred until the evolution of carbon dioxide stops. The mixture is cooled on an ice bath and 3.0 g (0.027 mole) of benzyl alcohol is added. The reaction is allowed to warm to room temperature and evaporated to dryness. The residue is extracted with ether-H2O. The ether layer is washed with 10% aqueous HCl, water, saturated sodium chloride, dried with sodium sulfate and evaporated to dryness affording 2-[5-(tetradecyloxy)-2-furoyl]acetic acid benzyl ester.

Workup

  1. temperatureThe mixture is cooled on an ice bath
  2. customevaporated to dryness
  3. extractionThe residue is extracted with ether-H2O
  4. washThe ether layer is washed with 10% aqueous HCl, water, saturated sodium chloride
  5. dry with materialdried with sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-8b9c49d6dc5a4632aaa39a2e0fa817ab
Source dataset
uspto-grants-1976_12
Patent number
US04000164

Reaction notes

Loading…