Ethyl Acetate → 2-Methyl-beta-[[4-(tetradecyloxy)phenyl]methyl]-1,3-dioxolane-2-propanol

HRID 235704Notes

Reaction equation

HRID 235704 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH2:13][CH:14]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:23][CH:22]=2)[C:15](OCC)=[O:16])[O:12][CH2:11][CH2:10][O:9]1.C(OCC)(=O)C.[OH-].[Na+]>CCOCC.O>[CH3:7][C:8]1([CH2:13][CH:14]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:25][CH:26]=2)[CH2:15][OH:16])[O:9][CH2:10][CH2:11][O:12]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 867412682-Methyl-alpha-[[4-(tetradecyloxy)phenyl]methyl]-1,3-dioxolane-2-propanoic acid, ethyl ester

Product 1

HCID 202193422-Methyl-beta-[[4-(tetradecyloxy)phenyl]methyl]-1,3-dioxolane-2-propanolYield 81.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of about 2.38 g of lithium aluminum hydride in about 40 ml of ether was added dropwise, over about 1/2 hour, a solution of about 20.5 g of 2-methyl-α-[[4-(tetradecyloxy)phenyl]methyl]-1,3-dioxolane-2-propanoic acid, ethyl ester in about 70 ml of ether at about 0° C. The mixture was stirred about 1/2 hour at room temperature, recooled to about 0° C. and about 10 ml of ethyl acetate, about one ml of water, about 2 ml of about 15% sodium hydroxide and about 3 ml of water were added dropwise. The mixture was filtered through celite, the solids were washed with ether and the ether removed from the combined solutions, which was then purified by HPLC, using the system hexane:ethyl acetate (about 3:7), giving a colorless oil which solidified on standing, giving about 15.28 g of the desired title compound, mp 28°-29° C.

Workup

  1. additionwas added dropwise, over about 1/2 hour
  2. customat about 0° C
  3. customrecooled to about 0° C.
  4. filtrationThe mixture was filtered through celite
  5. washthe solids were washed with ether
  6. customthe ether removed from the combined solutions, which
  7. customwas then purified by HPLC
  8. customethyl acetate (about 3:7), giving a colorless oil which

Sources & evidence

ORD record
ord-919f31e7683d4153ac8776bf16958fe9
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Reaction notes

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