4-[(Hexadecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane → 1-O-Hexadecylglycerol

HRID 881582Notes

Reaction equation

HRID 881582 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][O:8][CH2:9][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][CH2:23][CH3:24])[CH2:4][O:3]1>Cl>[CH2:9]([O:8][CH2:7][CH:5]([CH2:4][OH:3])[OH:6])[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][CH2:23][CH3:24]

Participants

3

Reactant 1

HCID 139162514-[(Hexadecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 727331-O-Hexadecylglycerol

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
120 °C

Procedure

To compound 1a (3.363 g) was added 10% HCl solution (40 mL) and refluxed at 120° C. for 30 min. The reaction mixture was then kept at RT for 24 hours. The white lumps formed were filtered. The filtrate was extracted with hexane (50 mL, 2×) and the extracts added to the white lumps after removal of solvent. It was dried in a vacuum dessicator for 24 hours to obtain 2a which was quantitative. 1H NMR (in CDCl3): δ in ppm 0.83-0.87 (3H, m), 1.23 (26H, m), 1.52-1.55 (2H, m), 2.67 (1H, D2O exchangeable), 3.42-3.51 (4H, m), 3.60-3.70 (2H, m), 3.84-3.85 (1H, m), 6.63-6.70 (1H, D2O exchangeable); 13C NMR (in CDCl3): δ in ppm 14.6, 23.1, 26.5, 29.8, 29.9, 30.0, 30.1, 30.2, 32.4, 64.5, 71.0, 72.3, 72.9.

Workup

  1. customThe white lumps formed
  2. filtrationwere filtered
  3. extractionThe filtrate was extracted with hexane (50 mL, 2×)
  4. additionthe extracts added to the white lumps
  5. customafter removal of solvent
  6. customIt was dried in a vacuum dessicator for 24 hours

Sources & evidence

ORD record
ord-d9b7c2f6b816449ea65267b469f67dd9
Source dataset
uspto-grants-2015_03
Patent number
US08993623B2

Reaction notes

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