Ethanol → HCID 54555720, compound

HRID 1076024Notes

Reaction equation

HRID 1076024 reaction equation
[O:1]=[C:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:3]=[CH:4][C:5]1[O:9][C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:7][CH:6]=1.[CH2:25](O)[CH3:26]>>[CH2:25]([O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:8]1[O:9][C:5]([CH:4]=[CH:3][C:2](=[O:1])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:6][CH:7]=1)[CH3:26]

Participants

3

Reactant 2

HCID 702EthanolHCID 54512710HCID 54512710, compound

Product 1

HCID 54555720HCID 54555720, compoundYield 79%

Procedure

A mixture of II (9.94 g, 0.0298 mole), ethanol (190 ml), and ethyl ether-borontrifluoride complex (0.97 g) was stirred and heated under reflux for 1.5 hours. After cooling, the reaction mixture was poured into ice-water (600 ml) and extracted with three 300-ml portions of ether. The combined ethereal extracts were washed with cold 10% sodium carbonate (100 ml) and then with two 200-ml portions of cold water. The ethereal solution was dried over magnesium sulfate and evaporated to dryness from a water bath (60°C), at last under 15 mm Hg. The residual yellow oil (9.84 g) was purified by distillation under nitrogen from a potassium acetatecoated flask giving 8.57 g (79%) of IV, b0.2 198°-201°C, nD25 1.5217.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling
  4. extractionextracted with three 300-ml portions of ether
  5. washThe combined ethereal extracts were washed with cold 10% sodium carbonate (100 ml)
  6. dry with materialThe ethereal solution was dried over magnesium sulfate
  7. customevaporated to dryness from a water bath (60°C)
  8. distillationThe residual yellow oil (9.84 g) was purified by distillation under nitrogen from a potassium acetatecoated flask

Sources & evidence

ORD record
ord-e537f6949d8f42cbbe0257ac2e215bc3
Source dataset
uspto-grants-1976_05
Patent number
US03954813

Reaction notes

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