Ethylene Glycol → HCID 14119832, compound

HRID 1836943Notes

Reaction equation

HRID 1836943 reaction equation
CC(C)([O-])C.[K+].Br[CH:8]1[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:10]2[CH2:9]1.Cl.[CH2:17]([OH:20])[CH2:18][OH:19]>>[OH:19][CH2:18][CH2:17][O:20][CH:8]1[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:10]2[CH2:9]1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 5685917-Bromobicyclo[4.2.0]octa-1,3,5-trieneHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 14119832HCID 14119832, compound

Conditions

Temperature
80 °C

Procedure

To 56.1 g of potassium t-butoxide, 150 ml of ethylene glycol was dropwise added in a stream of nitrogen to dissolve potassium t-butoxide completely. To the solution, 45.3 g of 1-bromobenzocyclobutene (synthesized according to a method of DeCamp et al., J. Org. Chem., 1981, 46, 3918) was dropwise added. After the addition was completed, the mixture was heated to 80° C., and stirred for 8 hours. The mixture was cooled to room temperature, and poured into ice-cold water. After adjusting pH to 6 with hydrochloric acid, an organic phase was extracted with ethyl acetate. After the solvent was distilled away, the residue was purified in a silica gel chromatography to obtain 20.6 g of 1-(2′-hydroxyethoxy)-benzocyclobutene.

Workup

  1. addition, 1981, 46, 3918) was dropwise added
  2. additionAfter the addition
  3. temperatureThe mixture was cooled to room temperature
  4. additionpoured into ice-cold water
  5. extractionan organic phase was extracted with ethyl acetate
  6. distillationAfter the solvent was distilled away
  7. customthe residue was purified in a silica gel chromatography

Sources & evidence

ORD record
ord-353fa5376396467ba0a8c3ae2fa37401
Source dataset
uspto-grants-2004_08
Patent number
US06780567B2

Reaction notes

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