Sodium Hydroxide → 3-Tetrahydropyranyloxyoxetane

HRID 1075310Notes

Reaction equation

HRID 1075310 reaction equation
C([O:4][CH2:5][CH:6]([O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)[CH2:7]Cl)(=O)C.[OH-].[Na+]>O>[O:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]1[O:9][CH:6]1[CH2:5][O:4][CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 190484163-Chloro-2-tetrahydropyranyloxy-1-propyl acetate

Product 1

HCID 540831123-TetrahydropyranyloxyoxetaneYield 100.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 476 g of crude 3-chloro-2-tetrahydropyranyloxy-1-propyl acetate was added 216 g (5.4 moles) of sodium hydroxide in 500 mL of water. The reaction mixture was heated at reflux for 17 hours. The upper organic layer was separated and taken up in 350 mL of methylene chloride. The methylene chloride solution was dried over sodium sulfate and solvent was removed in vacuo to leave 320.9 g of 3-tetrahydropyranyloxyoxetane: 1H NMR (CDCl3) δ1.63 (br. s, 6H, CH2); 3.2-4.4 (m, 2H, --OCH2); 4.47 (br. s, 1H, CH); 4.67 (br. s, 4H, O(CH2)); 5.17 (br, s, 1H, O--CH); IR (CH2Cl2) 2970, 2910 (C--H); 980 cm-1 (oxetane). Extraction of the aqueous layer with ether gave an additional 10.3 g for an overall crude yield of 331.2 g. 3-Tetrahydropyranyloxyoxetane distilled with some decomposition at 48°-65° (0.2 mm).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 17 hours
  3. customThe upper organic layer was separated
  4. dry with materialThe methylene chloride solution was dried over sodium sulfate and solvent
  5. customwas removed in vacuo

Sources & evidence

ORD record
ord-a2dd1de55f1442fba8ea25b076590d57
Source dataset
uspto-grants-1983_07
Patent number
US04395561

Reaction notes

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