Sodium Hydroxide → Ethyl 2,3-dihydro-2-vinyl-1H-indene-2-carboxylate

HRID 1494599

Reaction equation

HRID 1494599 reaction equation
[OH-].[Na+].Br[CH2:4][C:5]1[C:6]([CH2:11]Br)=[CH:7][CH:8]=[CH:9][CH:10]=1.[C:13]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:14][CH:15]=[CH2:16]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:15]([C:14]1([C:13]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][C:6]2[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:4]1)=[CH2:16]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 66665o-Bis(bromomethyl)benzeneHCID 74172Ethyl vinylacetate

Product 1

HCID 19828699Ethyl 2,3-dihydro-2-vinyl-1H-indene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent2×

Procedure

Tetrabutylammonium bromide (0.31 g) and 48% NaOH solution (9 ml) were added to a flask. α,α'-dibromo-o-xylene (5.0 g) in toluene (15 ml) was then added to the flask. The mixture was stirred and ethyl 3-butenoate (2.16 g) in toluene (15 ml) was added dropwise at room temperature. After the addition the temperature was slowly raised to +60° C. The mixture was stirred at this temperature for 3.5 hours and then cooled. The toluene layer was separated, washed with water and evaporated at reduced pressure to give the desired product.

Workup

  1. additionAfter the addition the temperature
  2. temperaturewas slowly raised to +60° C
  3. stirringThe mixture was stirred at this temperature for 3.5 hours
  4. temperaturecooled
  5. customThe toluene layer was separated
  6. washwashed with water
  7. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-fcd5f311a99c451cb83ce258f6480ff3
Source dataset
uspto-grants-1991_06
Patent number
US05026868

Linked notes

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