Hydrochloric Acid → 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzyl alcohol

HRID 982056Notes

Reaction equation

HRID 982056 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.Cl>CCOCC.O>[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:24]=[CH:23][C:19]([CH2:20][OH:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10314719Agn-190205HCID 21226445Aluminium lithium hydride

Product 1

HCID 539501414-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzyl alcoholYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of 15.8 g (48 millimoles) of 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzoic acid (Example 6) in 160 ml of absolute ether was added dropwise to a suspension of 1.9 g (49 millimoles) of lithium aluminum hydride in 150 ml of absolute ether. Thereafter, the mixture was stirred under reflux for 3 hours, after which 50 ml of ethyl acetate, 200 ml of water and 150 ml of 2N HCl were added dropwise in succession, and the phases were separated. The aqueous phase was extracted once again with ether, and the combined ether extracts were washed with water, dried over Na2SO4 and evaporated down. The oil which remained (17 g) was stirred with heptane, and the resulting crystals were filtered off under suction and dried. 7.2 g (48%) of the title compound of melting point 115°-117° C. were obtained in this manner.

Workup

  1. temperatureunder reflux for 3 hours
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted once again with ether
  4. washthe combined ether extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated down
  7. stirringwas stirred with heptane
  8. filtrationthe resulting crystals were filtered off under suction
  9. customdried

Sources & evidence

ORD record
ord-f5af234b3b13476db2939ebe82cc1982
Source dataset
uspto-grants-1991_02
Patent number
US04994489

Reaction notes

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