Hydrochloric Acid → HCID 22323773, compound

HRID 324235Notes

Reaction equation

HRID 324235 reaction equation
[CH3:1]/[C:2](/[CH:9]=[CH:10]/[CH:11]=[C:12](/[C:14]1[CH:23]=[CH:22][C:21]2[C:20]([CH3:25])([CH3:24])[CH2:19][CH:18]=[C:17]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)[C:16]=2[CH:15]=1)\[CH3:13])=[CH:3]\[C:4]([O:6]CC)=[O:5].CO.[Li+].[OH-].Cl>C1COCC1.CCOCC>[CH3:1]/[C:2](/[CH:9]=[CH:10]/[CH:11]=[C:12](/[C:14]1[CH:23]=[CH:22][C:21]2[C:20]([CH3:24])([CH3:25])[CH2:19][CH:18]=[C:17]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)[C:16]=2[CH:15]=1)\[CH3:13])=[CH:3]\[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 86586185HCID 86586185, compound2×

Product 1

HCID 22323773HCID 22323773, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (E,E,E)-3-methyl-7-(5,6-dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenyl)-2,4,6-octatrienoate (Compound 51) 85.0 mg, 0.20 mmol) in THF (1 ml) and methanol (1 ml) was added 12.0 mg (0.50 mmol) of LiOH (0.5 ml, 1M solution). The mixture was stirred for 6 hours, diluted with ether (60 ml), acidified with 10% HCl (1 ml). The solution was washed with water, and saturated aqueous NaCl, before being dried over MgSO4. Removal of the solvents under reduced pressure afforded the title compound as a solid, which was purified by recrystallization from acetone. 1H NMR (acetone-d6): δ 7.35-7.45 (2H, m), 7.19-7.28 (4H, m), 7.17 (1H, d, J=1.8 Hz), 7.09 (1H, dd, J=11.5, 15.1 Hz), 6.48 (1H, d, J=11.5 Hz), 6.42 (1H, d, J=15.1 Hz), 5.99 (1H, t, J=4.7 Hz), 5.82 (1H, s), 2.36 (3H, s), 2.33 (2H, d, J=4.7 Hz), 2.32 (3H, s), 2.13 (3H, s), 1.32 (6H, s).

Workup

  1. washThe solution was washed with water, and saturated aqueous NaCl
  2. dry with materialbefore being dried over MgSO4
  3. customRemoval of the solvents under reduced pressure

Sources & evidence

ORD record
ord-c5cc4c5c493a42bdb1d1bb9975a7d554
Source dataset
uspto-grants-2001_04
Patent number
US06218128B1

Reaction notes

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