Hydrochloric Acid → 1-(Hexadecyloxy)but-3-EN-2-OL

HRID 255963

Reaction equation

HRID 255963 reaction equation
[Mg].[CH:2](Br)=[CH2:3].[CH2:5]([O:21][CH2:22][CH:23]=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].Cl>O1CCCC1.BrC(Br)C.CCOCC>[CH2:5]([O:21][CH2:22][CH:23]([OH:24])[CH:2]=[CH2:3])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11641BromoetheneHCID 5462224Magnesium2×HCID 14785848(Hexadecyloxy) acetaldehyde

Product 1

HCID 139590711-(Hexadecyloxy)but-3-EN-2-OLYield 41.5%

Reagents, catalysts & solvents 3

HCID 112011,1-DibromoethaneCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a stirring mixture of 5.67 g of magnesium in 25 ml of tetrahydrofuran was added 10 drops of dibromoethane as an initiator. After the reaction began another 100 ml of tetrahydrofuran was added followed by the dropwise addition of a solution of 49.85 g of vinyl bromide in 250 ml of tetrahydrofuran at a rate to maintain reflux. After all of the magnesium had reacted, the solution was cooled to 0° C. and a solution of 44.2 g of (hexadecyloxy) acetaldehyde, prepared by the procedure of Example 3, in 175 ml of ether was added dropwise over 1/2 hour. After 1 hour at room temperature dilute hydrochloric acid was added. The tetrahydrofuran was removed and the residue was extracted with ether. The ether layer was washed with brine, dried and the solvent removed. The residue was purified by HPLC [hexane: ether (9:1), two columns, two passes] giving an oil which was distilled via a Kugelrohr apparatus (185°-190° C., 0.2 mm) giving a colorles oil which solidified on standing to give 20.17 g of the desired compound.

Workup

  1. additionwas added
  2. temperatureto maintain
  3. temperaturereflux
  4. additionwas added dropwise over 1/2 hour
  5. customThe tetrahydrofuran was removed
  6. extractionthe residue was extracted with ether
  7. washThe ether layer was washed with brine
  8. customdried
  9. customthe solvent removed
  10. customThe residue was purified by HPLC [hexane: ether (9:1), two columns, two passes]
  11. customgiving an oil which
  12. distillationwas distilled via a Kugelrohr apparatus (185°-190° C., 0.2 mm)
  13. customgiving a colorles oil which

Sources & evidence

ORD record
ord-41414b2cf6584599ac72779c5a79dd96
Source dataset
uspto-grants-1987_10
Patent number
US04699990

Linked notes

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