Cetyl Alcohol → 1-Chloro-3-(hexadecyloxy)propan-2-ol

HRID 1591025Notes

Reaction equation

HRID 1591025 reaction equation
[CH2:1]([OH:17])[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].[CH2:18]([CH:20]1[O:22][CH2:21]1)[Cl:19]>CCOCC>[CH2:1]([O:17][CH2:21][CH:20]([OH:22])[CH2:18][Cl:19])[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

4

Reactant 2

HCID 2682Cetyl AlcoholHCID 7835Epichlorohydrin

Product 1

HCID 124588591-Chloro-3-(hexadecyloxy)propan-2-olYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Hexadecanol (10.0 g, 0.0412 mole) and stannic chloride (0.04 g, 0.16 mmoles) were heated to 60° C. Epichlorohydrin (3.82 g, 0.0412 moles (was added over 1 hour and the reaction conditions kept constant for another hour. The hot product was extracted with 5% aqueous HCl and ether. The ether was concentrated to a white solid product (yield=75%).

Workup

  1. customthe reaction conditions
  2. waitkept constant for another hour
  3. extractionThe hot product was extracted with 5% aqueous HCl and ether

Sources & evidence

ORD record
ord-dfa04e0bc3564c4584fadab6cf12931e
Source dataset
uspto-grants-1993_04
Patent number
US05206020

Reaction notes

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