Methyl 3,3-Bis(4-chlorophenyl)propenoate → Methyl 3,3-Bis(4-chlorophenyl)propionate

HRID 1987264Notes

Reaction equation

HRID 1987264 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1>CO.Cl.[Pt](=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 44720501Methyl 3,3-Bis(4-chlorophenyl)propenoate

Product 1

HCID 22270432Methyl 3,3-Bis(4-chlorophenyl)propionate

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A suspension of methyl 3,3-bis(4-chlorophenyl)propenoate (Step A, 3.0 g, 14 mmol) and platinum dioxide (0.30 g) in MeOH (20 mL) and 2 M aqueous hydrochloric acid (1 mL) was degassed and filled with hydrogen with a balloon. After stirring at room temperature for 2 h, the reaction mixture was filtered through CELITE diatomaceous earth, and the filtrate was concentrated to dryness. The residue was dissolved in 50 mL ether and was concentrated with 20 g silica gel. The material was loaded onto a silica gel column, which was eluted with 10% ether in hexane to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.29-7.22 (m, 4H), 4.50 (t, 1H), 3.56 (s, 3H), 3.07 (d, 2H). LC-MS: m/e 309 (M+H)+ (4.1 min).

Workup

  1. customwas degassed
  2. additionfilled with hydrogen with a balloon
  3. filtrationthe reaction mixture was filtered through CELITE diatomaceous earth
  4. concentrationthe filtrate was concentrated to dryness
  5. dissolutionThe residue was dissolved in 50 mL ether
  6. concentrationwas concentrated with 20 g silica gel
  7. washwas eluted with 10% ether in hexane

Sources & evidence

ORD record
ord-3148f2a896aa4662a0cb193deb08bf47
Source dataset
uspto-grants-2009_06
Patent number
US07550489B2

Reaction notes

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