Acetone → HCID 54006541, compound

HRID 868442Notes

Reaction equation

C([O:8][CH2:9][CH:10]([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:11][CH2:12][C:13](=[O:15])[CH3:14])C1C=CC=CC=1.O.C(O)C.CC(C)=O>C(O)(=O)C.[C].[Pd]>[CH2:18]([O:17][CH2:16][CH:10]([O:11][CH2:12][C:13](=[O:15])[CH3:14])[CH2:9][OH:8])[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]

Participants

Conditions

Temperature: 50 °C

Procedure

Hydrogenolysis of 6.5 g (13.3 mmole) of 1-benzyl-3-octadecyl-2-(2-oxopropyl)glycerol was carried out in a mixture of 100 ml of acetic acid, 20 ml of water and 20 ml of ethanol using 2.5 g of 10% palladium carbon (50% wet) at ambient temperature under atmospheric pressure. 100 ml of acetone was added and the mixture was heated up to 50° C. Then, the catalyst was filtered off and 100 ml of 2-methylpropanol was added. Furthermore, the mixture was concentrated to dryness under reduced pressure. 100 ml of toluene was added to the residue and the mixture was again concentrated to dryness. 70 ml of hexane was added to the residue, and the crystals precipitated were collected by filtration to give 3.9 g (yield: 74%) of the above-identified compound.

Workup

filtrationThen, the catalyst was filtered off
addition100 ml of 2-methylpropanol was added
concentrationFurthermore, the mixture was concentrated to dryness under reduced pressure
addition100 ml of toluene was added to the residue
concentrationthe mixture was again concentrated to dryness
addition70 ml of hexane was added to the residue
customthe crystals precipitated
filtrationwere collected by filtration

Sources & evidence

ORD record: ord-3814a72e645c4fa1b4b2efe2e7a0319d
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04778912

Reaction notes

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