Acetyl chloride → Methyl 2-Benzyloxy-2-methylpropionate

HRID 34741Notes

Reaction equation

HRID 34741 reaction equation
[CH2:1]([O:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](Cl)(=O)C>CO>[CH2:1]([O:8][C:9]([CH3:14])([CH3:13])[C:10]([O:12][CH3:15])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 113445632-(Benzyloxy)-2-methylpropanoic acid

Product 1

HCID 13716841Methyl 2-Benzyloxy-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Benzyloxy-2-methylpropionic acid (4.4 g., 0.0023 mol) was dissolved in 50 ml. of methanol treated with acetyl chloride (1.61 ml., 1.78 g., 0.0023 mol), stirred for 16 hours, stripped to an oil, taken up in 75 ml. ethyl acetate, washed 1×50 ml. saturated NaHCO3 and 1×50 ml. brine, dried over MgSO4 and stripped to yield purified title product as a second oil, 4.22 g.; 1H-nmr 1.5 (s, 6H), 3.8 (s, 3H), 4.5 (s, 2H), 7.3-7.5 (m, 5H).

Workup

  1. washethyl acetate, washed 1×50 ml
  2. dry with materialbrine, dried over MgSO4
  3. customto yield
  4. custompurified title product as a second oil, 4.22 g

Sources & evidence

ORD record
ord-58c1fb5a854b4ef99bbf80686c0873fb
Source dataset
uspto-grants-1988_08
Patent number
US04762921

Reaction notes

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