Ethanol → HCID 4770937, compound

HRID 1503629Notes

Reaction equation

HRID 1503629 reaction equation
[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].C([O-])([O-])=O.[K+].[K+].[CH2:19]([O:21][C:22](=[O:25])[CH2:23]Br)[CH3:20].C(O)C>CC(C)=O>[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[O:12][CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:25]

Participants

6

Reactant 4

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 296223-Chloro-4-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 4770937HCID 4770937, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound was prepared according to general procedure E with 5-chlorovanillin (2.7 mmol) in dry acetone (25 ml), anhydrous K2CO3 (3.5 mmol), and ethylbromoacetate (4.05 mmol) at reflux for 1 h30. Ethanol was added and evaporated by azeotropic distillation with ethylbromoacetate. 957 mg of crude product were obtained and purified by silica gel chromatography (eluent dichloromethane). 330 mg of purified compound were obtained (45% yield). 1H NMR (250 MHz, CD3COCD3): δ 1.27 (t, J=7.2 Hz, 3H), 3.98 (s, 3H), 4.22 (q, J=7.2 Hz, 2H), 4.87 (s, 2H), 7.50 (s, 1H), 7.58 (s, 1H), 9.90 (s, 1H) 13C NMR (126 MHz, CD3COCD3): δ 15.1, 57.5, 62.1, 70.5, 112.3, 125.8, 128.9, 134.0, 149.7, 154.5, 169.5, 191.2. MS (ESI): m/z 272.9 and 274.9 [M+H]+.

Workup

  1. customThe compound was prepared
  2. temperatureat reflux for 1 h30
  3. customevaporated by azeotropic distillation with ethylbromoacetate
  4. custom957 mg of crude product were obtained
  5. custompurified by silica gel chromatography (eluent dichloromethane)

Sources & evidence

ORD record
ord-3e32abf67a474517b9f85f8af5d32284
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

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