Hydrochloric Acid → 2-[5-[(5-Oxo-2-propyl-5,6,7,8-tetrahydro-1-naphthalenyl)oxy]pentyloxy]benzenepropanoic acid

HRID 327973Notes

Reaction equation

HRID 327973 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[C:28]2[CH2:27][CH2:26][CH2:25][C:24](=[O:29])[C:23]=2[CH:22]=[CH:21][C:20]=1[CH2:30][CH2:31][CH3:32].[OH-].[Na+].Cl.CCOCC>CO.O>[O:29]=[C:24]1[CH2:25][CH2:26][CH2:27][C:28]2[C:19]([O:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[CH2:5][CH2:4][C:3]([OH:33])=[O:2])=[C:20]([CH2:30][CH2:31][CH3:32])[CH:21]=[CH:22][C:23]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 53803245HCID 53803245, compound

Product 1

HCID 199220172-[5-[(5-Oxo-2-propyl-5,6,7,8-tetrahydro-1-naphthalenyl)oxy]pentyloxy]benzenepropanoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The 2-[5-[(5-oxo-2-propyl-5,6,7,8-tetrahydro-1-naphthalenyl)oxy]pentyloxy]benzenepropanoic acid methyl ester from the preceding example (1.35 g; 2.99 mmol) and 8 mL of 1N aqueous sodium hydroxide in 15 mL of methanol was stirred and refluxed for 1.5 hr. After being cooled, the resulting solution was diluted with water and acidified with 3N HCl. Work-up with ether in the usual manner gave 1.3 g (100%) 2-[5-[(5-oxo-2-propyl-5,6,7,8-tetrahydro-1-naphthalenyl)oxy]pentyloxy]benzenepropanoic acid as an orange oil.

Workup

  1. temperaturerefluxed for 1.5 hr
  2. temperatureAfter being cooled

Sources & evidence

ORD record
ord-dd294e758d934d3ba271014cf5c94727
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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