Hydrochloric Acid → tert-Butyl 12-hydroxy-4,7,10-trioxadodecanoate

HRID 1479428Notes

Reaction equation

HRID 1479428 reaction equation
[CH2:1]([OH:10])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][OH:9].[C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])[CH:12]=[CH2:13].[Na].Cl>C1COCC1.[Na]>[OH:10][CH2:1][CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:13][CH2:12][C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8172Triethylene GlycolHCID 15458tert-Butyl acrylateHCID 5360545Sodium

Product 1

HCID 3625858tert-Butyl 12-hydroxy-4,7,10-trioxadodecanoateYield 88.4%

Reagents, catalysts & solvents 2

HCID 5360545SodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To triethyleneglycol (17.6 g, 117.20 mmol, 3.00 equiv) in anhydrous THF (70 mL), was added sodium (30 mg, 1.25 mmol, 0.03 equiv). Tert-butyl acrylate (5.0 g, 39.01 mmol, 1.00 equiv) was added after the sodium had dissolved. The resulting solution was stirred overnight at room temperature and then neutralized with 1.0 N hydrogen chloride. After removal of the solvent, the residue was suspended in 50 mL of brine and extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with saturated brine and dried over anhydrous sodium sulfate. After evaporation of the solvent, the tert-butyl 3-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)propanoate (9.6 g) was isolated as a colorless oil, which was used directly for the next reaction step without further purification.

Workup

  1. dissolutionhad dissolved
  2. customAfter removal of the solvent
  3. extractionextracted with 3×50 mL of ethyl acetate
  4. washThe combined organic layers were washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-9e8e791462734c79942486ee3ee7ed1c
Source dataset
uspto-grants-2016_08
Patent number
US09408840B2

Reaction notes

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