tert-Butanol → tert-Butyl 4-acetylbenzoate

HRID 2269804Notes

Reaction equation

HRID 2269804 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:13](O)([CH3:16])([CH3:15])[CH3:14].CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 79724-MethylmorpholineHCID 114704-Acetylbenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 13844704tert-Butyl 4-acetylbenzoateYield 59%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-acetylbenzoic acid (3.9 g) in anhydrous methylene chloride (120 ml) are added 4-dimethylaminopyridine (1.5 g), t-butyl alcohol (4.6 ml), N-methylmorpholine (3.4 ml) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.0 g) under ice cooling. The mixture is stirred under ice cooling for six hours and under water cooling overnight. The reaction mixture is concentrated under reduced pressure, water is added to the concentrate, and the whole is extracted with ether. The organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 3.13 g (59%) of t-butyl 4-acetylbenzoate as crystals.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, water
  2. additionis added to the concentrate
  3. extractionthe whole is extracted with ether
  4. washThe organic layer is washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9b497b57ef4e45c6a08d9e59235e847e
Source dataset
uspto-grants-2001_12
Patent number
US06329547B1

Reaction notes

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