Ethanol → HCID 86715428, compound

HRID 1503633Notes

Reaction equation

HRID 1503633 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[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>[CH3:1][C:2]1[CH:9]([C:8]([CH3:11])([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 752223,5-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 86715428HCID 86715428, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound was prepared according to general procedure E with 3,5-dimethyl-4-hydroxybenzaldehyde (3.3 mmol) in dry acetone (20 ml), anhydrous K2CO3 (4.3 mmol), and ethylbromoacetate (5 mmol) at reflux for 1 h. Ethanol was added and evaporated by azeotropic distillation with ethylbromoacetate. 774 mg of crude product were obtained and purified by silica gel chromatography (eluent dichloromethane). 580 mg of purified compound were obtained (74% yield). 1H NMR (250 MHz, CDCl3): δ 1.26 (t, J=7.2 Hz, 3H), 2.33 (s, 6H), 4.23 (q, J=7.2 Hz, 2H), 4.42 (s, 2H), 7.50 (s, 2H), 9.82 (s, 1H) 13C NMR (126 MHz, CDCl3): δ 15.2, 17.4, 62.2, 70.1, 131.6, 132.8, 133.8, 161.7, 169.5, 192.1

Workup

  1. customThe compound was prepared
  2. temperatureat reflux for 1 h
  3. customevaporated by azeotropic distillation with ethylbromoacetate
  4. custom774 mg of crude product were obtained
  5. custompurified by silica gel chromatography (eluent dichloromethane)

Sources & evidence

ORD record
ord-b0bcc8c2670a450180095667e7943daf
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

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