Hydrochloric Acid → 5-(2-chloroethylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

HRID 1899755Notes

Reaction equation

HRID 1899755 reaction equation
[ClH:1].[CH2:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2.[CH2:18]=O>C(O)(=O)C>[Cl:1][CH2:18][CH:2]=[C:3]1[C:4]2[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=2[CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 46413975-Methylene-10,11-dihydro-5H-dibenzo[a,d][7]annulene

Product 1

HCID 124928075-(2-chloroethylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as in (2) in Example 2, hydrogen chloride gas was bubbled into the mixture of 20.6 g (0.1 mol) of 10,11-dihydro-5-methylene-5H-dibenzo[a,d]cycloheptene (4c), 41 g of acetic acid, and 4.5 g (0.15 mol) of paraformaldehyde. After reaction was conducted, the reaction product was extracted with toluene, neutralized with a saturated sodium bicarbonate solution, and washed with water. Further, this product was dried with sodium sulfate anhydride, concentrated and then recrystallized from hexane to obtain 23.4 g of the compound (5c). Theoretical yield, 92.0%; m.p., 103°-104° C.

Workup

  1. customAfter reaction
  2. extractionthe reaction product was extracted with toluene
  3. washwashed with water
  4. dry with materialFurther, this product was dried with sodium sulfate anhydride
  5. concentrationconcentrated
  6. customrecrystallized from hexane

Sources & evidence

ORD record
ord-e39ac3429f864fc284b6213bee447027
Source dataset
uspto-grants-1996_11
Patent number
US05573878

Reaction notes

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