Ethanol → 5-(Hydroxymethyl)-5-[(octadecyloxy)methyl]oxolan-2-one

HRID 652983Notes

Reaction equation

HRID 652983 reaction equation
C([O:8][CH2:9][C:10]1([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[O:14][C:13](=[O:15])[CH2:12][CH2:11]1)C1C=CC=CC=1.C(O)C.[H][H]>[Pd].O>[OH:8][CH2:9][C:10]1([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[O:14][C:13](=[O:15])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 702EthanolHCID 13914376HCID 13914376, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 139143775-(Hydroxymethyl)-5-[(octadecyloxy)methyl]oxolan-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture containing 10.7 g (21.83 mmol) of the compund prepared in (e) above, 300 ml of a mixture of ethyl alcohol and water in a ratio of 9:1 and 1.5 g of 5% palladium on carbon (50% water content) was placed in a pressure bottle and hydrogenated at b 40° C. under a pressure of 50 lbs. of hydrogen until uptake was complete. The catalyst was then filtered off and the filtrate concentrated in vacuo. The residue was crystallized from methanol to yield a solid.

Workup

  1. additionA mixture containing 10.7 g (21.83 mmol) of the compund
  2. customwas placed in a pressure bottle and hydrogenated at b 40° C. under a pressure of 50 lbs
  3. filtrationThe catalyst was then filtered off
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was crystallized from methanol
  6. customto yield a solid

Sources & evidence

ORD record
ord-bf3d0c72b45743eaa485b94f5122d21a
Source dataset
uspto-grants-1987_06
Patent number
US04673672

Reaction notes

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