1,4-Bis(bromomethyl)benzene → 2-(bromomethyl)-2-ethylpropane-1,3-diol

HRID 2286827Notes

Reaction equation

HRID 2286827 reaction equation
P1(OCC)[O:6][CH2:5][C:4]([CH2:9][CH3:10])([CH2:7][Br:8])[CH2:3][O:2]1.BrCC1C=CC(CBr)=CC=1>>[CH2:9]([C:4]([CH2:7][Br:8])([CH2:5][OH:6])[CH2:3][OH:2])[CH3:10]

Participants

3

Conditions

Temperature
100 °C

Procedure

2-Ethyl-2-bromomethyltrimethylene ethyl phosphite (IV), 97 grams, 0.372 mole and α,α'-dibromo-p-xylene, 48.9 grams, 0.186 mole, were mixed in a 500 ml. flask equipped with an air condenser and a nitrogen inlet tube. The mixture was slowly heated to 100° C., at which time the reaction was completed, leaving a white solid. The solid was washed with two 100 ml. portions of benzene-acetone (50/50) and then ground in a morter to a fine powder. The powder was boiled in benzene-acetone (50/50) for several minutes, cooled to 10° C., filtered and dried in a vacuum oven at 50° C. for 12 hours. There was obtained 109 grams of product, m.p. 242° C.

Workup

  1. customflask equipped with an air condenser and a nitrogen inlet tube
  2. customleaving a white solid
  3. washThe solid was washed with two 100 ml
  4. waitThe powder was boiled in benzene-acetone (50/50) for several minutes
  5. temperaturecooled to 10° C.
  6. filtrationfiltered
  7. customdried in a vacuum oven at 50° C. for 12 hours

Sources & evidence

ORD record
ord-e3e46900c34a41ba8b014e714f83178d
Source dataset
uspto-grants-1981_05
Patent number
US04268459

Reaction notes

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