Hydrochloric Acid → 5',6'-Dihydro-5',5'-dimethyl-8'-(4-methylphenyl)-[2,2'-binaphthalene]6-carboxylic acid

HRID 324246Notes

Reaction equation

HRID 324246 reaction equation
C(C1C2C(=CC=CC=2)C=CC=1C1C=CC2C(C)(C)CC=C(C3C=CC(C)=CC=3)C=2C=1)C.[CH3:32][C:33]1([CH3:65])[CH2:42][CH:41]=[C:40]([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=2)[C:39]2[CH:38]=[C:37]([C:50]3[CH:59]=[CH:58][C:57]4[C:52](=[CH:53][CH:54]=[C:55]([C:60]([O:62]CC)=[O:61])[CH:56]=4)[CH:51]=3)[CH:36]=[CH:35][C:34]1=2.[OH-].[Na+].Cl>CCO>[CH3:32][C:33]1([CH3:65])[CH2:42][CH:41]=[C:40]([C:43]2[CH:44]=[CH:45][C:46]([CH3:49])=[CH:47][CH:48]=2)[C:39]2[CH:38]=[C:37]([C:50]3[CH:59]=[CH:58][C:57]4[C:52](=[CH:53][CH:54]=[C:55]([C:60]([OH:62])=[O:61])[CH:56]=4)[CH:51]=3)[CH:36]=[CH:35][C:34]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15870725Ethyl 5',6'-dihydro-5',5'-dimethyl-8'-(4-methylphenyl)-[2,2'-binaphthalene]-6-carboxylateHCID 131722496Ethyl 5',6'-dihydro-5',5'-dimethyl-8'-(4-methylphenyl)-2,2'-binaphthalene

Product 1

HCID 158707265',6'-Dihydro-5',5'-dimethyl-8'-(4-methylphenyl)-[2,2'-binaphthalene]6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 5′,6′-dihydro-5′,5′-dimethyl-8′-(4-methylphenyl)-2,2′-binaphthalene]-6-carboxylate (Compound 64) 0.19 g, 0.43 mmol), EtOH (8 ml) and 1N aqueous NaOH (2 ml) was heated to 60° C. for 3 hours. The solution was cooled to 0° C. and acidified with 1N aqueous HCl. The product was extracted into ethyl acetate, and the organic layers combined, washed with water, brine, dried (MgSO4), filtered and the solvent removed in-vacuo. The residue was recrystalized from THF/ethyl acetate at 0° C. to give 35 mg of pure material. The mother liquor was concentrated under reduced pressure and the residue purified by silica gel chromatography (100% ethyl acetate) to give an additional 125 mg of the title compound (overall yield=160 mg, 90%) as a colorless solid. 1H NMR (DMSO-d6) δ 8.57 (s, 1H), 8.11 (d, 1H, J=8.7 Hz), 7.96-7.82 (overlapping d's, 3H),7.65 (d, 2H, J=7.6 Hz), 7.50 (d, 1H, J=7.9 Hz), 7.28 (s, 1H), 7.26 (d, 2H, J=8.3 Hz), 7.21 (d, 2H, J=8.3 Hz), 6.01 (t, 1H, J=4.5 Hz), 3.34 (br s, 1H), 2.31 (s, 3H), 2.31 (d, 2H, J=4.5 Hz), 1.31 (s, 6H).

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed in-vacuo
  6. customThe residue was recrystalized from THF/ethyl acetate at 0° C.

Sources & evidence

ORD record
ord-1bc1a5e9fc2f476db7b70c5fa8921db1
Source dataset
uspto-grants-2001_04
Patent number
US06218128B1

Reaction notes

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