Hydrochloric Acid → HCID 14233258, compound

HRID 1761735Notes

Reaction equation

HRID 1761735 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:20]=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:30][Mg]Br.Cl>O1CCCC1.CCOCC>[CH2:1]([O:17][CH2:18][CH:19]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:20]([OH:21])[CH3:30])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21242399HCID 21242399, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 14233258HCID 14233258, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 10 g of 3-(hexadecyloxy)-2-(phenylmethoxy)-propanal in 120 ml of dry tetrahydrofuran, under argon, at 5° C., was added dropwise 16.4 ml of 3M methyl magnesium bromide in ether at a rate to maintain the temperature below 8° C. The mixture was stirred at 5° C. for 15 minutes, then at room temperature for 3 hours, recooled to 5° C. and 50 ml of 1N hydrochloric acid was added dropwise at a rate to maintain the temperature below 10° C. The organic phase was separated and the aqueous phase extracted with ether. The ether extract was combined with the organic phase, washed with saturated aqueous sodium bicarbonate, then saturated brine, dried and taken to dryness. The residue was dissolved in petroleum ether, washed with saline, dried and taken to dryness. The residue was purified by HPLC using ether:hexane (1:5), giving 6.16 g of the desired compound as a pale yellow oil.

Workup

  1. temperatureto maintain the temperature below 8° C
  2. waitat room temperature for 3 hours
  3. customrecooled to 5° C.
  4. temperatureto maintain the temperature below 10° C
  5. customThe organic phase was separated
  6. extractionthe aqueous phase extracted with ether
  7. extractionThe ether extract
  8. washwashed with saturated aqueous sodium bicarbonate
  9. dry with materialsaturated brine, dried
  10. dissolutionThe residue was dissolved in petroleum ether
  11. washwashed with saline
  12. customdried
  13. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-9d25191c7a7942c2a672ce9a01942227
Source dataset
uspto-grants-1989_05
Patent number
US04827011

Reaction notes

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