Water → HCID 19764346, compound

HRID 248153Notes

Reaction equation

HRID 248153 reaction equation
[CH2:1]=[C:2]([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][CH2:18][CH2:19][CH3:20])[CH2:3]O.N1C=CC=CC=1.P(Br)(Br)[Br:28].O>CCOCC>[Br:28][CH2:3][C:2]([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][CH2:18][CH2:19][CH3:20])=[CH2:1]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24614Phosphorus tribromideHCID 11358027HCID 11358027, compound

Product 1

HCID 19764346HCID 19764346, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-15 °C

Procedure

A mixture of 20 g of 2-methylene-1-octadecanol, 150 ml of ether and 12.6 ml of pyridine is cooled to -15° C. in an ice-methanol bath. A solution of 7.3 ml of phosphorous tribromide in 50 ml of ether is added slowly over 1 hour, and the mixture is allowed to warm to room temperature overnight. The mixture is recooled to 0° C., 1.9 ml of water added and then allowed to warm to room temperature over 6 hours. The mixture is washed, filtered and evaporated, to give 19.2 g of the desired compound as a clear oil.

Workup

  1. temperatureto warm to room temperature overnight
  2. customis recooled to 0° C.
  3. temperatureto warm to room temperature over 6 hours
  4. washThe mixture is washed
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7760bd2ef3d24e18a60e45e8859b9bc6
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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