Methanol → HCID 53800149, compound

HRID 1076023Notes

Reaction equation

HRID 1076023 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.[CH3:25]O>>[CH3:25][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

Participants

3

Reactant 2

HCID 887MethanolHCID 54512710HCID 54512710, compound

Product 1

HCID 53800149HCID 53800149, compoundYield 79%

Procedure

II (2.52 g, 0.00755 mole), methanol (30 ml), and ethyl ether-borontrifluoride complex (0.24 g) were stirred and heated under reflux for 1 hour. After cooling, the reaction mixture was poured into ice-water (150 ml) and extracted with two 80-ml portions of ether. The combined ethereal extracts were washed with cold 10% sodium carbonate (50 ml) and then with two 50-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. Distillation under nitrogen of the residual oil (2.46 g) gave 2.07 g (79%) of III, b0.3 202°-204°C, nD25 1.5262.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. extractionextracted with two 80-ml portions of ether
  5. washThe combined ethereal extracts were washed with cold 10% sodium carbonate (50 ml)
  6. dry with materialThe ethereal solution was dried over magnesium sulfate
  7. customevaporated to dryness from a water bath (60°C)
  8. distillationDistillation under nitrogen of the residual oil (2.46 g)

Sources & evidence

ORD record
ord-fde44b350b694317a14a1d08a266cf25
Source dataset
uspto-grants-1976_05
Patent number
US03954813

Reaction notes

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