Hydrochloric Acid → trans-2,5-Bis-(hydroxymethyl)-1,4-dioxane

HRID 572646Notes

Reaction equation

HRID 572646 reaction equation
C([O:4][CH2:5][C@H:6]1[CH2:11][O:10][C@H:9]([CH2:12][O:13]C(=O)C)[CH2:8][O:7]1)(=O)C.O1CCOCC1.Cl>CO>[OH:4][CH2:5][C@H:6]1[CH2:11][O:10][C@H:9]([CH2:12][OH:13])[CH2:8][O:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68794212HCID 68794212, compound

Product 1

HCID 14275539trans-2,5-Bis-(hydroxymethyl)-1,4-dioxaneYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of trans-2,5-bis-(acetoxymethyl)-1,4-dioxane (14.5 g, 220 mmol, Preparation #11: Step a) in MeOH (40 mL) was added 4N.dioxane.HCl (20 mL, 220 mmol) and heated to reflux for 1 h. Then reaction mixture was cooled to RT and the solvents were evaporated under reduced pressure. The resulting oily residue was triturated with 10% EtOAc in hexane (3×50 mL) to afford trans-2,5-bis-(hydroxymethyl)-1,4-dioxane 9.0 g (97%) as brown solid; 1H NMR (400 MHz, CDCl3): δ 3.85-3.82 (m, 2H), 3.67-3.52 (m, 10H), 2.05 (bs, 1H); MS: m/z 149.1 (m+H)+.

Workup

  1. custom14.5 g, 220 mmol, Preparation #11
  2. temperatureto reflux for 1 h
  3. customThen reaction mixture
  4. customthe solvents were evaporated under reduced pressure
  5. customThe resulting oily residue was triturated with 10% EtOAc in hexane (3×50 mL)

Sources & evidence

ORD record
ord-cc307a32e4634effa35c79abebc1efc8
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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