Water → 2-[(Hexadecyloxy)methyl]-4-penten-1-ol

HRID 248158

Reaction equation

HRID 248158 reaction equation
[H-].[Na+].[CH2:3]([OH:8])CCC=C.[CH2:9]([O:25][C:26]1[CH:35]=[C:34](C)[CH:33]=[CH:32]C=1S([O-])(=O)=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].O>CN(C)C=O.O1CCCC1>[CH2:9]([O:25][CH2:26][CH:35]([CH2:34][CH:33]=[CH2:32])[CH2:3][OH:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 131814-Penten-1-OLHCID 24758Sodium hydrideHCID 19764414HCID 19764414, compound

Product 1

HCID 147858282-[(Hexadecyloxy)methyl]-4-penten-1-olYield 10.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of 19.1 g of 50% sodium hydride under argon in 300 ml of N,N-dimethylformamide is added dropwise over a period of 1 hour, with stirring a solution of 37 g of 4-penten-1-ol, 2-methanol (prepared as described by B. K. Wasson, et. al., J. Chem. Soc., 39, 923 (1961)) in 200 ml of tetrahydrofuran. After stirring another 30 minutes, 126.34 g of hexadecyloxytosylate is added followed by 500 ml of tetrahydrofuran. This mixture is stirred for 2.5 hours, then heated to 80° C. for 20 minutes and then at room temperature overnight. Water is added and the mixture extracted with ether. The ether extract is dried and then evaporated. The residue is distilled using a Kugelrohr. The fraction distilling at 200°-210° C. 1 mm is collected, purified by chromatography and then redistilled, to give 11.35 g of the desired compound.

Workup

  1. additionis added dropwise over a period of 1 hour
  2. stirringThis mixture is stirred for 2.5 hours
  3. customat room temperature
  4. customovernight
  5. extractionthe mixture extracted with ether
  6. extractionThe ether extract
  7. customis dried
  8. customevaporated
  9. distillationThe residue is distilled
  10. distillationThe fraction distilling at 200°-210° C
  11. custom1 mm is collected
  12. custompurified by chromatography
  13. distillationredistilled

Sources & evidence

ORD record
ord-3402bc0cebab48a88639ec72101a89f7
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Linked notes

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