Hydrochloric Acid → 4-[1(Tol-4-yl)-3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoic Acid

HRID 1375262Notes

Reaction equation

HRID 1375262 reaction equation
[C:1]1([CH3:34])[CH:6]=[CH:5][C:4]([C:7]2[C:20]3[C:11](=[CH:12][C:13]4[C:18]([CH:19]=3)=[C:17]([C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=3)[CH:16]=[CH:15][CH:14]=4)[C:10]([CH3:33])([CH3:32])[CH2:9][CH:8]=2)=[CH:3][CH:2]=1.CO.[Li+].[OH-].Cl>C1COCC1.CCOCC>[C:1]1([CH3:34])[CH:2]=[CH:3][C:4]([C:7]2[C:20]3[C:11](=[CH:12][C:13]4[C:18]([CH:19]=3)=[C:17]([C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:30][CH:31]=3)[CH:16]=[CH:15][CH:14]=4)[C:10]([CH3:32])([CH3:33])[CH2:9][CH:8]=2)=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 24821095Ethyl 4-[1(tol-4-yl)3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoate2×

Product 1

HCID 248210964-[1(Tol-4-yl)-3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoic Acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a degassed solution of ethyl 4-[1(tol-4-yl)3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoate (Compound 1, 35 mg, 0.08 mmol), in THF (1.5. mL) and MeOH (1.5 mL) was added LiOH (1M solution in water, 0.3. mL, 0.3 mmol). The mixture was stirred at ambient temperature for 16 hours, diluted with ether (60 mL). The mixture was acidified with 10% HCl to pH 4, the product was isolated as an ether insoluble white solid.

Sources & evidence

ORD record
ord-315a9d34d30f4efb81931d05c9e46ed7
Source dataset
uspto-grants-2007_01
Patent number
US07166726B2

Reaction notes

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