Ethyl chloroacetate → Ethyl 2-(4-formyl-3,5-dimethylphenoxy)acetate

HRID 1514866Notes

Reaction equation

HRID 1514866 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([CH3:11])[CH:3]=1.Cl[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]([CH:6]=[O:7])=[C:8]([CH3:10])[CH:9]=1)[CH3:18]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 10796Cesium carbonateHCID 5910722,6-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 54425547Ethyl 2-(4-formyl-3,5-dimethylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxy-2,6-dimethyl-benzaldehyde (87 mg), ethyl chloroacetate (85 mg) and Cs2CO3 (375 mg) in acetone (4 mL) was stirred at room temperature for 16 h. The mixture was concentrated, diluted with water, and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give (4-formyl-3,5-dimethyl-phenoxy)-acetic acid ethyl ester: MS (m/z) 237 (M+1); 1H NMR (CDCl3, 400 MHz) δ 10.48 (s, 1H), 6.59 (s, 2H), 4.66 (s, 2H), 4.29 (q, 2H), 2.60 (s, 6H), 3.29 (t, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4585454b511e4cff9a3cf18120235448
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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