Dichloromethane → 2-Phenylindan

HRID 2351547Notes

Reaction equation

HRID 2351547 reaction equation
ClCCl.[OH-].[Na+].[CH2:6]([C:13]#N)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[C:7]1([CH:6]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8794Phenylacetonitrile2×HCID 14798Sodium Hydroxide2×

Product 1

HCID 896382-PhenylindanYield 115.4%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalyst2×HCID 962WaterSolvent

Procedure

To a stirred two phase solution of dichloromethane (1 L) and 15% NaOH (750 mL) were added alpha, alpha,-di-bromo-o-xylene (100 g, 0.38 mol), benzyl cyanide (44.3 g, 0.38 mol) and benzyltriethylammonium chloride (17.2 g, 0.075 mol). The two phase solution was vigorously stirred at ambient temperature for 48 hours, at which time benzyl cyanide (20 g, 0.17 mol), benzyltriethylammonium chloride (9.0 g, 0.039 mol), and 15% NaOH (300 mL) were added. The mixture was stirred for an additional 48 hours. The reaction was poured into water (1 L) and extracted with ether (2.5 L). The organic solution was washed with water (3×1 L), brine (500 mL), dried over magnesium sulfate and the solvents evaporated. Vacuum distillation of the residue gave 42.6 g of 2,3-dihydro-2-phenyl-1H-indene- 2-carbontrile, bp 166°-168° C. (5 mm), Lit. bp 160°-180° C. ( 1 mm), as a colorless oil.

Workup

  1. additionwere added
  2. extractionextracted with ether (2.5 L)
  3. washThe organic solution was washed with water (3×1 L), brine (500 mL)
  4. dry with materialdried over magnesium sulfate
  5. customthe solvents evaporated
  6. distillationVacuum distillation of the residue

Sources & evidence

ORD record
ord-906f446fe28f42b6b6725a605aa02e43
Source dataset
uspto-grants-1989_10
Patent number
US04873241

Reaction notes

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