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

HRID 1721756
Notes
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Reaction equation

HRID 1721756 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 463.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 2-chloro-9-formylanthracene (described in example 1b) (100.0 g, 0.415 mol) and vinyl acetate (400 ml, 374 g, 4.34 mol) 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 mol) of the 2-chloro-9-formylanthracene, 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.). 1H NMR (CDCl3) 10.58 (s) and 10.64 (s, 1H), 7.63 (m) and 7.76 (d, J=1.5 Hz, 1H), 7.15-7.36 (m, 6H), 5.46 (m, 1H), 4.29 (s, 1H), 2.55 (m, 1H), 1.88 (s) and 1.91 (s, 1H), 1.55 (m, 1H).

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-fc76781d8fe043e8a6cb17b85d905179
Source dataset
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05512575

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes