Ethyl bromoacetate → Diethyl 2,2'-[(4-formyl-1,2-phenylene)bis(oxy)]diacetate

HRID 2425028Notes

Reaction equation

HRID 2425028 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH2:11]([O:13][C:14](=[O:17])[CH2:15]Br)[CH3:12].C([O-])([O-])=O.[K+].[K+].[CH3:24][CH2:25][O:26][C:27]([CH3:29])=[O:28]>>[CH2:11]([O:13][C:14](=[O:17])[CH2:15][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[O:1][CH2:29][C:27]([O:26][CH2:25][CH3:24])=[O:28])[CH3:12]

Participants

5

Reactant 4

HCID 7748Ethyl bromoacetateHCID 87683,4-DihydroxybenzaldehydeHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 15237909Diethyl 2,2'-[(4-formyl-1,2-phenylene)bis(oxy)]diacetate

Procedure

3,4-Dihydroxy-benzaldehyde was treated with 2-bromo-acetic acid ethyl ester in the presence of K2CO3 and processed as described in the synthesis of example 20a. The crude product was purified using flash chromatography (silica gel, 30-50% EtOAc in PE 60-80° C.). Yield, 87%; mp, 56° C. (EtOAc-PE 60-80° C.); MS (EI): 310 (M+), 237, 163, 149; analysis: C15H18O7, 0.5H2O requires C, 56.37; H, 5.95; found: C, 56.72; H, 5.79%.

Workup

  1. customas described in the synthesis of example 20a
  2. customThe crude product was purified
  3. customflash chromatography (silica gel, 30-50% EtOAc in PE 60-80° C.)
  4. customYield

Sources & evidence

ORD record
ord-4e7035bf0fe94e4a9d0db4feb72c8367
Source dataset
uspto-grants-2011_06
Patent number
US07964628B2

Reaction notes

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