Ethanol → HCID 21410119, compound

HRID 1076816Notes

Reaction equation

HRID 1076816 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.[CH2:6](O)[CH3:7].C(O[CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[C:21]=[O:22])[C:13]1=[O:23])C.[OH-:24].[Na+]>O>[Br:1][CH2:2][CH2:3][CH2:4][C:14]1([C:21]([O:22][CH2:6][CH3:7])=[O:24])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][C:13]1=[O:23]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 86732897HCID 86732897, compound

Product 1

HCID 21410119HCID 21410119, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 1,3-dibromopropane (175 ml.) and ethanol (250 ml.) is added dropwise a solution of 1-ethoxy-carbonyl-2-indanone (51 g.) and sodium hydroxide (10 g.) in 500 ml. of ethanol and 200 ml. of water. The solution is refluxed for 5 hours and cooled. The bottom layer is separated and the upper layer is diluted with water and extracted with two 100 ml. portions of carbon tetrachloride. The combined lower layers were washed with 5% aqueous sodium hydroxide and water then concentrated and distilled to give, after a small forecut, the title product (40.3 g.) with b.p. 155°-165° at 0.5 mm.

Workup

  1. temperatureThe solution is refluxed for 5 hours
  2. temperaturecooled
  3. customThe bottom layer is separated
  4. additionthe upper layer is diluted with water
  5. extractionextracted with two 100 ml
  6. washwere washed with 5% aqueous sodium hydroxide and water
  7. concentrationthen concentrated
  8. distillationdistilled
  9. customto give

Sources & evidence

ORD record
ord-aaa6ac4ddebf4ab5ac2cfa4e06f3b010
Source dataset
uspto-grants-1976_05
Patent number
US03957872

Reaction notes

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