1,2-Bis(2-chloroethoxy)ethane → 3-{2-[2-(2-Chloroethoxy)ethoxy]ethoxy}-4,5-dimethoxybenzaldehyde

HRID 1510970Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[OH:13].Cl[CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][Cl:23].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:13][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:11][CH3:12])[C:3]=1[O:2][CH3:1])[CH:7]=[O:8]

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 500 mg (2.75 mmol) 4,5-dimethoxy-3-hydroxybenzaldehyde 1 and 860 μl (1.03 g, 5.50 mmol) 1,2-bis(2-chloroethoxy)ethane in 20 ml DMF was treated with 2.24 g (6.88 mmol) caesium carbonate and heated to 55° C. for 20 hrs. After cooling the mixture was poured into 100 ml of ice water and extracted with chloroform. The organic extracts were washed twice with 50 ml of water and with brine, dried over sodium sulfate and evaporated. The resulting yellow oil was flash-chromatographed (petroleum ether/ethyl acetate 2/1) to yield 3-{2-[2-(2-chloroethoxy)ethoxy]ethoxy}-4,5-dimethoxybenzaldehyde (730 mg, 2.20 mmol, 80%), which was directly used for the next synthesis step.

Workup

temperatureAfter cooling the mixture
extractionextracted with chloroform
washThe organic extracts were washed twice with 50 ml of water and with brine
dry with materialdried over sodium sulfate
customevaporated
customThe resulting yellow oil was flash-chromatographed (petroleum ether/ethyl acetate 2/1)

Sources & evidence

ORD record: ord-188516f93ea24b198ee9512e3cd43a0e
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08212058B2

Reaction notes

Loading…