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

HRID 610315

Reaction equation

HRID 610315 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 pH 5. 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-238680ad6c1f4fd8aa601d5ddbff7685
Source dataset
uspto-grants-1999_12
Patent number
US05998471

Linked notes

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