Methanol → HCID 54544527, compound

HRID 2071669Notes

Reaction equation

HRID 2071669 reaction equation
[OH:1][C:2]([CH3:25])([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][CH2:4][CH:5]1[O:9][CH:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:7][CH2:6]1.[CH3:26]O>>[CH3:26][O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:8]1[CH2:7][CH2:6][CH:5]([CH2:4][CH2:3][C:2]([OH:1])([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:9]1

Participants

3

Reactant 2

HCID 887MethanolHCID 21412035HCID 21412035, compound

Product 1

HCID 54544527HCID 54544527, compoundYield 98%

Procedure

XI (1.78 g, 0.00500 mole), methanol (25 ml), and ethyl ether-borontrifluoride complex (0.1 ml) were stirred and heated under reflux for 1 hour. After cooling, the reaction mixture was poured into ice-water (200 ml) and extracted with ether (50 + 50 + 25 ml). The combined ethereal extracts were washed with cold 2% aqueous sodium hydrogen carbonate (50 ml) and water (50 ml). The ethereal solution was dried over sodium sulfate and evaporated to dryness from a water bath (60° C, 10 mm Hg). The residual yellowish oil (1.95 g) was distilled under reduced pressure to give 1.82 g (98%) of XII as a colourless oil, b0.03 160°-170° C, nD25 1.4625.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. extractionextracted with ether (50 + 50 + 25 ml)
  5. washThe combined ethereal extracts were washed with cold 2% aqueous sodium hydrogen carbonate (50 ml) and water (50 ml)
  6. dry with materialThe ethereal solution was dried over sodium sulfate
  7. customevaporated to dryness from a water bath (60° C, 10 mm Hg)
  8. distillationThe residual yellowish oil (1.95 g) was distilled under reduced pressure

Sources & evidence

ORD record
ord-e0008efc87ba46cba0e1911f5968dedf
Source dataset
uspto-grants-1977_09
Patent number
US04048198

Reaction notes

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