HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 2209611
Notes
Print preview

Reaction equation

HRID 2209611 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.). 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-0965e8d958124c4b8e8b404396dcd0c2
Source dataset
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05455246

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes