Solketal → (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl acetate

HRID 1437588Notes

Reaction equation

HRID 1437588 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>CN(C1C=CN=CC=1)C.ClCCl>[C:10]([O:8][CH2:7][CH:5]1[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]1)(=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 7528SolketalHCID 7918Acetic Anhydride

Product 1

HCID 252333(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 28.1 g (212 mmol) of 2,2-dimethyl-1,3-dioxolane-4-methanol and 44 g (361 mmol) of DMAP in 1 L of dichloromethane was added 36 mL (382 mmol) of acetic anhydride dropwise. The resulting mixture was stirred at rt for 0.5 h. The reaction mixture was then quenched with NH4Cl (aq), the organic layer separated and washed with saturated NaHCO3. The organic layer was then dried (Na2SO4), filtered and concentrated in vacuo to give an oil which was used without further purification. 1H NMR (500 MHz, acetone-d6): δ 4.30-4.25 (m, 1H), 4.09-4.01 (m, 1H), 3.72 (dd, 1H), 2.01 (s, 3H), 1.33 (s, 3H), 1.27 (s, 3H).

Workup

  1. customThe reaction mixture was then quenched with NH4Cl (aq)
  2. customthe organic layer separated
  3. washwashed with saturated NaHCO3
  4. dry with materialThe organic layer was then dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give an oil which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-d0c38f3d127e4eb3854c9aa39861d659
Source dataset
uspto-grants-2009_11
Patent number
US07622501B2

Reaction notes

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