Sulfuric Acid → HCID 15735698, compound

HRID 1885552Notes

Reaction equation

HRID 1885552 reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[O:22])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.S(=O)(=O)(O)O>C(OCC)C.O1CCCC1>[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([OH:22])[CH2:3][CH:2]=[CH2:1])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 1573569710-PhenyldecanalHCID 178455850HCID 178455850, compound

Product 1

HCID 15735698HCID 15735698, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution of 1M allyl magnesium bromide in diethyl ether was added dropwise, under nitrogen, a solution of 18.2 g of 10-phenyldecanal (prepared as in Step 1) in 200 ml of dry tetrahydrofuran. The reaction mixture was stirred at about 5° for 15 minutes, at room temperature for 1 hour, and then at reflux for 15 minutes. The reaction mixture was cooled to room temperature and poured into a mixture of 400 g of ice and 40 ml of 9M sulfuric acid. Upon standing the mixture separated into aqueous and organic layers. The organic layer was stirred for 15 min with solid sodium bicarbonate and then concentrated. The aqueous layer was extracted with diethyl ether (2×200 ml) and the extracts were combined with the concentrated organic layer. The combined organics were washed with water (300 ml) and a half-saturated aqueous solution of sodium chloride (300 ml), dried over anhydrous magnesium sulfate, filtered and concentrated to an oil. High pressure liquid chromatography of the oil using 10% diethyl ether/hexane as the eluent gave 6.98 g (30%) of 13-phenyl-1-tridecen-4-ol as an oil.

Workup

  1. temperatureat reflux for 15 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customseparated into aqueous and organic layers
  4. stirringThe organic layer was stirred for 15 min with solid sodium bicarbonate
  5. concentrationconcentrated
  6. extractionThe aqueous layer was extracted with diethyl ether (2×200 ml)
  7. washThe combined organics were washed with water (300 ml)
  8. dry with materiala half-saturated aqueous solution of sodium chloride (300 ml), dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-a34eb90ec9fd489a86154e440104aae1
Source dataset
uspto-grants-1992_09
Patent number
US05145844

Reaction notes

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