Hydrochloric Acid → Ro 14-6113

HRID 986688Notes

Reaction equation

HRID 986688 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[C:10](/[C:12]2[CH:21]=[CH:20][C:19]3[C:18]([CH3:23])([CH3:22])[CH2:17][CH2:16][C:15]([CH3:25])([CH3:24])[C:14]=3[CH:13]=2)\[CH3:11])=[CH:5][CH:4]=1.Cl>CO>[OH:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[C:10](/[C:12]2[CH:21]=[CH:20][C:19]3[C:18]([CH3:23])([CH3:22])[CH2:17][CH2:16][C:15]([CH3:25])([CH3:24])[C:14]=3[CH:13]=2)\[CH3:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 138854251,2,3,4-tetrahydro-6-[(E)-p-methoxy-alpha-methylstyryl]-1,1,4,4-tetramethylnaphthalene

Product 1

HCID 6439236Ro 14-6113Yield 113.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

3.8 g (11 mmol) of (E)-1-(4-methoxyphenyl)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-propene from Example 1 were suspended in 50 ml of methanol saturated with hydrogen chloride, and the suspension was stirred for 20 minutes at 60° C. Thereafter, the reaction solution was poured into about 150 ml of ice water and extracted with three times 100 ml of methyl tert-butyl ether. The organic phase was washed with twice 100 ml of saturated sodium chloride solution and twice with water, dried over Na2SO4 and evaporated down to give 4 g of a solid crude product. This crude product was recrystallized from isopropanol to give 1.5 g of the title compound of melting point 138°-140° C.

Workup

  1. extractionextracted with three times 100 ml of methyl tert-butyl ether
  2. washThe organic phase was washed with twice 100 ml of saturated sodium chloride solution and twice with water
  3. dry with materialdried over Na2SO4
  4. customevaporated down

Sources & evidence

ORD record
ord-64bf0f7a76084361aa55df72c69347f3
Source dataset
uspto-grants-1987_12
Patent number
US04714786

Reaction notes

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