Hydrochloric Acid → HCID 13711790, compound

HRID 648765Notes

Reaction equation

HRID 648765 reaction equation
[CH2:1]([O:17][C:18]1[C:19](=[O:32])[CH:20]=[C:21]([CH2:24][O:25]C2CCCCO2)[O:22][CH:23]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl.CCCCCC>C1COCC1.CCOCC>[OH:25][CH2:24][C:21]1[O:22][CH:23]=[C:18]([O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:19](=[O:32])[CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 13711801HCID 13711801, compound

Product 1

HCID 13711790HCID 13711790, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-hexadecyloxy-2-tetrahydro pyranyloxymethyl-4pyrone (1.1 g, 2.5 mmol) and HCl (10% in H2O, 10 ml) in THF (30 ml) was stirred at 25° overnight. TLC (ETAC/hexane: 3/7) indicated reaction was complete. The solution was diluted with ether (200 ml), washed with H2O (3×50 ml), 10% NaHCO3 (1×50 ml), sat'd NaCl (1×100 ml), dried (K2CO3) and concentrated to provide 0.88 g (98%) of 2-hydroxymethyl-5-hexadecyloxy-4-pyrone as a pure white solid mp 68.0°-69.5°.

Workup

  1. customreaction
  2. washwashed with H2O (3×50 ml), 10% NaHCO3 (1×50 ml), sat'd NaCl (1×100 ml)
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c6f20b2843eb47ef83a8e27489e21f37
Source dataset
uspto-grants-1988_04
Patent number
US04735964

Reaction notes

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