Water → 3-(Hexadecylthio)-1-propanol

HRID 248170Notes

Reaction equation

HRID 248170 reaction equation
[BH4-].[Li+].[CH2:3]([S:19][CH2:20][CH2:21][C:22](OCC)=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O>O1CCCC1.Cl>[CH2:3]([S:19][CH2:20][CH2:21][CH2:22][OH:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 19764352Ethyl 3-(hexadecylthio)propanoate

Product 1

HCID 178317033-(Hexadecylthio)-1-propanolYield 99.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 147 mg of lithium borohydride in 20 ml of tetrahydrofuran is added slowly with stirring 2.4 g of ethyl 3-(hexadecylthio)propanoate. The mixture is refluxed for 18 hours and poured into water. A few drops of hydrochloric acid is added followed by ether extraction. The organic layer is dried and evaporated to give 2.1 g of the desired product.

Workup

  1. temperatureThe mixture is refluxed for 18 hours
  2. extractionfollowed by ether extraction
  3. customThe organic layer is dried
  4. customevaporated

Sources & evidence

ORD record
ord-0b3b8887de5b4ea48f366a80854b492f
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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