Benzyl Alcohol → HCID 53990429, compound

HRID 438022Notes

Reaction equation

HRID 438022 reaction equation
CCCC[CH:5]([O:15][C:16]1(C(CC(O)=O)=O)[S:20][CH:19]=[CH:18][CH2:17]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:27](=[O:29])=[O:28].[CH2:30](O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[CH2:30]([O:28][C:27](=[O:29])[CH2:6][C:5]([C:19]1[S:20][C:16]([O:15][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:17][CH:18]=1)=[O:15])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 280Carbon DioxideHCID 68122688HCID 68122688, compound

Product 1

HCID 53990429HCID 53990429, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10.4 g (0.027 mole) of 2-(5-tetradecyloxy)thenoylacetic acid, 4.4 g (0.027 mole) of N,N'-carbonyldiimidazole, and anhydrous tetrahydrofuran is stirred until the evolution of carbon dioxide gas stops. The mixture is cooled on an ice bath, in 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, then water, then saturated sodium chloride, dried with sodium sulfate and evaporated to dryness to give 5-tetradecyloxythen-2-oylacetic acid benzyl ester.

Workup

  1. additionis added
  2. customevaporated to dryness
  3. extractionThe residue is extracted with ether-H2O
  4. washThe ether layer is washed with 10% aqueous HCl
  5. dry with materialwater, then saturated sodium chloride, dried with sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-9b4f6c6476ea46b1be1fa39eb534d584
Source dataset
uspto-grants-1977_06
Patent number
US04032647

Reaction notes

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