tert-Butanol → HCID 10889004, compound

HRID 704897Notes

Reaction equation

HRID 704897 reaction equation
[I-].ClC1C=CC=C[N+]=1C.[C:10]([OH:20])(=[O:19])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH2:12].[C:21](O)([CH3:24])([CH3:23])[CH3:22].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)C.O>[C:13]1([C:11](=[CH2:12])[C:10]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 68114Atropic acidHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 10889004HCID 10889004, compoundYield 54.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A stirred suspension of 2-chloro-1-methylpyridinium iodide (3.28 g, 12.8 mmol) in toluene (20 mL) was treated under an atmosphere of nitrogen with atropic acid (1.80 g, 12.2 mol) treated with tert-butanol (0.92 mL, 11.8 mmol), treated with triethylamine (3.6 mL, 25.8 mmol), heated under reflux for 2 hours, cooled to room temperature and treated with water (100 mL) and diethyl ether (100 mL). The layers were separated and the aqueous layer extracted with diethyl ether (50 mL). The organic phases were combined, washed with water (100 mL), dried (MgSO4), evaporated in vacuo, and the residue purified by chromatography [silica; hexane-ethyl acetate (20:1)] to give tert-butyl 2-phenylpropenoate (1.32 g) as an oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with diethyl ether (50 mL)
  5. washwashed with water (100 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customthe residue purified by chromatography [silica; hexane-ethyl acetate (20:1)]

Sources & evidence

ORD record
ord-05f034be382d4854981e23d9d8fdf8cb
Source dataset
uspto-grants-1991_01
Patent number
US04988814

Reaction notes

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