Ethanol → HCID 86715427, compound

HRID 1503632Notes

Reaction equation

HRID 1503632 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:11])[C:9]=1[OH:10])[CH:5]=[O:6].[C:12]([O-])([O-])=[O:13].[K+].[K+].[CH2:18]([O:20][C:21](=[O:24])[CH2:22]Br)[CH3:19].C(O)C>CC(C)=O>[Cl:1][C:2]1[CH:9]([C:8]([Cl:11])([O:13][CH3:12])[CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1)[O:10][CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:24]

Participants

6

Reactant 4

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 168393,5-Dichloro-4-hydroxybenzaldehyde

Product 1

HCID 86715427HCID 86715427, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound was prepared according to general procedure E with 3,5-dichloro-4-hydroxybenzaldehyde (1.6 mmol) in dry acetone (15 ml), anhydrous K2CO3 (2.1 mmol), and ethylbromoacetate (2.4 mmol) at reflux for 1 h. Ethanol was added and evaporated by azeotropic distillation with ethylbromoacetate. 354 mg of crude product were obtained and purified by silica gel chromatography (eluent dichloromethane). 264 mg of purified compound were obtained (60% yield). 1H NMR (500 MHz, CD3COCD3): δ 1.32 (t, J=7.2 Hz, 3H), 4.30 (q, J=7.2 Hz, 2H), 4.74 (s, 2H), 7.82 (s, 2H), 9.67 (s, 1H) 13C NMR (126 MHz, CD3COCD3): δ 15.0, 62.3, 70.8, 131.2, 131.4, 135.4, 156.4, 168.4, 190.5

Workup

  1. customThe compound was prepared
  2. temperatureat reflux for 1 h
  3. customevaporated by azeotropic distillation with ethylbromoacetate
  4. custom354 mg of crude product were obtained
  5. custompurified by silica gel chromatography (eluent dichloromethane)

Sources & evidence

ORD record
ord-589c4641c16d48e4ab8bc0df6d648486
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

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