Acetyl chloride → Acetate

HRID 1827489Notes

Reaction equation

HRID 1827489 reaction equation
[C:1]([OH:6])#[C:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[C:9](Cl)(=[O:11])[CH3:10]>C1COCC1>[CH2:1]([OH:6])[C:2]#[C:3][CH2:4][OH:5].[CH3:10][C:9]([O-:11])=[O:5]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 13931173Butyne-1,4-diol

Product 2

HCID 175AcetateHCID 80662-Butyne-1,4-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of butyne-1,4-diol (5 g, 58 mmol) in dry THF at room temperature (RT) was added portion-wise sodium hydride (60% dispersion in oil, 2.32 g, 58 mmol). After 4.3 hr, acetyl chloride (4.12 mL, 58 mmol) was added. After stirring at RT for 22 hr, the mixture was concentrated under reduced pressure. The residue was concentrated twice from toluene before purification on silica gel using ethyl acetate/dichloromethane (1:3) as eluent to give 2-Butyne-1,4-diol, monoacetate as an oil in 49% yield. 1H NMR (DMSO-d6) δ 5.23 (1H, bs), 4.70 (2H, t, J=1.8 Hz), 4.09 (2H, s), 2.03 (3H, s).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. concentrationThe residue was concentrated twice from toluene before purification on silica gel

Sources & evidence

ORD record
ord-2a2ba96c895043838ce63fb58e0669db
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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