Ethanol → HCID 10899886, compound

HRID 1088006Notes

Reaction equation

HRID 1088006 reaction equation
[CH3:1][O:2][C:3]([CH3:9])([CH3:8])[CH2:4][CH2:5][CH:6]=O.C(OCC)(=O)[CH2:11][C:12]([CH3:14])=O.N1CCCC[CH2:20]1.[CH2:25]([OH:27])[CH3:26]>>[CH3:1][O:2][C:3]([CH3:9])([CH3:8])[CH2:4][CH2:5][CH:6]1[CH2:14][C:12]([CH3:11])=[CH:20][C:25](=[O:27])[CH2:26]1

Participants

5

Reactant 4

HCID 702EthanolHCID 8082Piperidine2×HCID 8868Ethyl AcetoacetateHCID 118294744-Methoxy-4-methylpentanal

Product 1

HCID 10899886HCID 10899886, compound

Procedure

To a stirred mixture of 4-methoxy-4-methylpentanal (60 g, 0.46 mol) and ethyl acetoacetate (156 g, 1.2 mol) at 5~C was added a 21% solution of piperidine in ethanol (4.1 mL). Further additions (4×18 mL) of the piperidine solution were made at about 24 hour intervals. The mixture was heated at reflux for 7 hours and concentrated to about 200 mL volume. Methanol (420 mL), water (420 mL) and sodium hydroxide (24 g) were added and the resulting mixture was heated at reflux 16 hours. Workup gave 3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohex-5-en-1-one bp0.1 135-140 ~C (69.2 g); NMR(CDC13)δ 1.2(s,6H), 0.9-1.6(m,5H), 1.9(s,3H), 5.9(brs,1H); IR(neat) 2975, 2930, 1675, 1640, 1380, 1080 cm-1 ; MS(m/e) 43, 73, 81, 109, 122, 163, 196.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 7 hours
  3. concentrationconcentrated to about 200 mL volume
  4. additionMethanol (420 mL), water (420 mL) and sodium hydroxide (24 g) were added
  5. temperaturethe resulting mixture was heated
  6. temperatureat reflux 16 hours

Sources & evidence

ORD record
ord-8f96f965d6274cad8e0b59ab8feae3be
Source dataset
uspto-grants-1990_10
Patent number
US04960946

Reaction notes

Loading…