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Methanol → 3-Acetoxy-3-methyl-2-butanone

HRID 1796032
Notes
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Reaction equation

HRID 1796032 reaction equation
[OH:1][C:2]([CH3:7])([CH3:6])[C:3](=[O:5])[CH3:4].C(N(CC)CC)C.[C:15](OC(=O)C)(=[O:17])[CH3:16].CO>ClCCl.CN(C)C1C=CN=CC=1.CCOCC>[CH3:6][C:2]([O:1][C:15](=[O:17])[CH3:16])([CH3:7])[C:3](=[O:5])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 82613-Hydroxy-3-methyl-2-butanoneHCID 8471Triethylamine

Product 1

HCID 123997123-Acetoxy-3-methyl-2-butanoneYield 94%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridine
Catalyst
HCID 3283Diethyl EtherSolvent
HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-hydroxy-3-methyl-2-butanone (10.75 ml, 100 mmol) and triethylamine (21 ml, 150 mmol) in dichloromethane (125 ml) was treated with acetic anhydride (11.8 ml, 125 mmol) then with 4-dimethylaminopyridine (610 mg, 5 mmol) and the reaction was stirred at ambient temperature for 14 h. Methanol (10 ml) was added and stirring continued for 30 min before concentrating the reaction in vacuo. The residue was dissolved in ether (300 ml) and washed with 0.5N hydrochloric acid (2×300 ml), water, saturated aqueous sodium hydrogencarbonate, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to afford acetic acid 1,1-dimethyl-2-oxopropyl ester as a yellow liquid (13.5 g, 94%): δH (400 MHz, CDCl3) 1.46 (6H, s), 2.09 (3H, s), 2.12 (3H, s).

Workup

  1. concentrationbefore concentrating
  2. customthe reaction in vacuo
  3. washwashed with 0.5N hydrochloric acid (2×300 ml), water, saturated aqueous sodium hydrogencarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-57c3f331802040498a1da23d7531a242
Source dataset
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07030128B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes