Vinyl Acetate → 12-Acetoxy-2-chloro-9-formyl-9,10-dihydro-9,10-ethanoanthracene

HRID 862719Notes

Reaction equation

HRID 862719 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([CH:16]=[O:17])[C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[C:18]([O:21][CH:22]=[CH2:23])(=[O:20])[CH3:19]>C(OCC)C>[C:18]([O:21][CH:22]1[C:5]2([CH:16]=[O:17])[C:6]3[C:11]([CH:12]([C:13]4[CH:14]=[CH:15][C:2]([Cl:1])=[CH:3][C:4]=42)[CH2:23]1)=[CH:10][CH:9]=[CH:8][CH:7]=3)(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 133753992-Chloro-9-formylanthracene2×

Product 1

HCID 1969867512-Acetoxy-2-chloro-9-formyl-9,10-dihydro-9,10-ethanoanthraceneYield 69.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 2-chloro-9-anthraldehyde, prepared as in Example 1c, (100.0 g, 0.415 moles) and vinyl acetate (400 ml, 374 g, 4.34 moles) was placed in a stainless steel bomb (PARR) and heated at 200° C. (sand bath temp.) for 24 h, then cooled. The reaction mixture was concentrated on the rotary evaporator to remove the excess vinyl acetate, leaving the crude product as a tan crystalline solid. The crude product from several batches, which consumed 670.0 g (2.78 moles) of 2-chloro-9-anthraldehyde, was pooled. Trituration with diethyl ether (1.0 L) gave an off-white crystalline solid which was collected by filtration, washed with diethyl ether (2×300 ml), then vacuum dried to afford 629.0 g (69.1%) of the title compound (mp 145°-153° C.).

Workup

  1. temperaturecooled
  2. concentrationThe reaction mixture was concentrated on the rotary evaporator
  3. customto remove the excess vinyl acetate
  4. customleaving the crude product as a tan crystalline solid
  5. filtrationwas collected by filtration
  6. washwashed with diethyl ether (2×300 ml)
  7. customvacuum dried

Sources & evidence

ORD record
ord-e45f9587fd4b45bea61630df0f09633e
Source dataset
uspto-grants-1998_02
Patent number
US05719166

Reaction notes

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