4-(3-Hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid → 4-[3-Oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid

HRID 840439Notes

Reaction equation

HRID 840439 reaction equation
[OH:1][CH:2]([C:14]1[CH:23]=[CH:22][C:21]2[C:20]([CH3:25])([CH3:24])[CH2:19][CH2:18][C:17]([CH3:27])([CH3:26])[C:16]=2[CH:15]=1)[C:3]#[C:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1>[O-2].[Mn+2].ClCCl>[O:1]=[C:2]([C:14]1[CH:23]=[CH:22][C:21]2[C:20]([CH3:25])([CH3:24])[CH2:19][CH2:18][C:17]([CH3:27])([CH3:26])[C:16]=2[CH:15]=1)[C:3]#[C:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([OH:11])=[O:10])=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 152858234-(3-Hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid

Product 1

HCID 152858244-[3-Oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

500 mg (1.38 mmol) of 4-(3-hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid, 50 ml of dichloromethane and 2.4 g (27.6 mmol) of manganese oxide were introduced into a round-bottomed flask which was placed in an ultrasonic bath for 4 hours. The reaction mixture was filtered, the filtrate was evaporated and the residue was purified by simple filtration through silica in ethyl ether. 90 mg (18%) of the expected compound, with a melting point of 208°-209° C., were recovered.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. filtrationthe residue was purified by simple filtration through silica in ethyl ether
  4. custom90 mg (18%) of the expected compound, with a melting point of 208°-209° C., were recovered

Sources & evidence

ORD record
ord-b635c15a598a47f3b8d362fcef05b99d
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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