Hydrochloric Acid → 4-[(5,6,7,8-Tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoic acid

HRID 277525

Reaction equation

HRID 277525 reaction equation
[OH:1][CH:2]1[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:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[Li+].[OH-].Cl>C1COCC1.CO.CCOCC.CCOC(C)=O>[OH:1][CH:2]1[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:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=3)[CH:5]=[CH:4][C:3]1=2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 15391671Ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate2×

Product 1

HCID 183145914-[(5,6,7,8-Tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

110 mg (0.31 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 9) in a mixture of THF and methanol was refluxed with 1 ml (1 mmol) of LiOH (1M aqueous solution). Thereafter the mixture was diluted with Et2O:EtOAc (1:1), and acidified with aqueous HCl to pH5. The organic phase was separated, washed (water and brine), dried (MgSO4) to yield the title compound.

Workup

  1. customThe organic phase was separated
  2. washwashed (water and brine)
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-711df7b430b147e4b0f7f92f153a5364
Source dataset
uspto-grants-2002_03
Patent number
US06355806B1

Linked notes

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