4-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)benzoic acid → p-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl) benzyl alcohol

HRID 1647838Notes

Reaction equation

HRID 1647838 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][C:8]([C:18]4[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=4)=[CH:9]3)=[CH:4][C:3]1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].[Na].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[K+]>C1COCC1>[CH3:1][C:2]1([CH3:27])[CH2:15][CH2:14][C:13]([CH3:16])([CH3:17])[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][C:8]([C:18]4[CH:26]=[CH:25][C:21]([CH2:22][OH:23])=[CH:20][CH:19]=4)=[CH:9]3)=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 1193424-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl)benzoic acidHCID 5360545SodiumHCID 6100505Dipotassium 2,3-dihydroxybutanedioateHCID 21226445Aluminium lithium hydride

Product 1

HCID 53945834p-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl) benzyl alcoholYield 58.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

300 mg (0.83 mmole) of p-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl) benzoic acid obtained in Example III above are dissolved in THF. 48 mg (1.25 mmoles) of LiAlH4 are added and the mixture is stirred initially for 15 minutes at ambient temperature and then for 10 minutes at reflux. The mixture is then left to stand until its temperature returns to ambient temperature. 28 μl of a saturated solution of sodium and potassium tartrate are then added. The mixture is then filtered and the THF is evaporated. The resulting residue is taken up in hexane and the precipitate that forms is filtered, yielding 167 mg (57% yield) of the expected alcohol which melts at 131° C.

Workup

  1. temperaturefor 10 minutes at reflux
  2. waitThe mixture is then left
  3. customto stand until its temperature returns to ambient temperature
  4. filtrationThe mixture is then filtered
  5. customthe THF is evaporated
  6. filtrationthe precipitate that forms is filtered

Sources & evidence

ORD record
ord-54655304375f47999cf715034a7ca9fe
Source dataset
uspto-grants-1995_07
Patent number
US05434180

Reaction notes

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