Sodium hydride → 2-Methyl-alpha-[[4-(tetradecyloxy)phenyl]methyl]-1,3-dioxolane-2-propanoic acid, ethyl ester

HRID 235703

Reaction equation

HRID 235703 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:5][CH:4]=1.[CH2:24]1[O:36][C:27]([CH3:35])([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:26][CH2:25]1.[H-].[Na+]>O1CCCC1>[CH3:35][C:27]1([CH2:28][CH:29]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:5][CH:4]=2)[C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:26][CH2:25][CH2:24][O:36]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 70332Ethyl 2-methyl-1,3-dioxolane-2-propionateHCID 100228401-(Bromomethyl)-4-(tetradecyloxy)benzene

Product 1

HCID 867412682-Methyl-alpha-[[4-(tetradecyloxy)phenyl]methyl]-1,3-dioxolane-2-propanoic acid, ethyl esterYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of about 33 g of 1-(bromomethyl)-4-(tetradecyloxy)benzene, about 16.2 g of ethyl levulinate ethylene ketal, about 4.54 g of about 50% sodium hydride and about 350 ml of tetrahydrofuran was refluxed with stirring, under argon for about 18 hours and then filtered through celite. The solvent was removed and the residue was dissolved in ether. The ether solution was washed with aqueous monobasic sodium phosphate, dried and the solvent removed. The residue was subjected to high performance liquid chromatography (HPLC), using the system hexane:ethyl acetate (about 9:1), giving about 22.1 g of the desired title compound as a light yellow oil).

Workup

  1. temperaturewas refluxed
  2. filtrationfiltered through celite
  3. customThe solvent was removed
  4. dissolutionthe residue was dissolved in ether
  5. washThe ether solution was washed with aqueous monobasic sodium phosphate
  6. customdried
  7. customthe solvent removed

Sources & evidence

ORD record
ord-95bfe5bf32f649c2b074aa3df909609f
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Linked notes

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