Hydrochloric Acid → HCID 67086895, compound

HRID 2365576Notes

Reaction equation

HRID 2365576 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH2:23][C@@H:24]4[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25]4)[CH:18]=3)[CH:13]=2)=[CH:6][CH:5]=1.[OH-].[Li+].Cl>C1COCC1.O>[CH3:29][C:26]1([CH3:30])[O:25][C@H:24]([CH2:23][O:22][C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[C:12]([CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:31])=[O:2])=[CH:5][CH:6]=2)[CH:21]=[CH:20]3)[CH2:28][O:27]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67120697HCID 67120697, compound

Product 1

HCID 67086895HCID 67086895, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 4-[6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-naphthalen-2-ylmethoxy]-benzoic acid methyl ester (0.46, 1.09 mmol) in THF/water (10 ml of a 1:1 mixture) is added lithium hydroxide (0.15 g, 3.57 mmol). The reaction mixture is stirred at room temperature overnight, then at 70° C. for 24 h. The reaction mixture is cooled to room temperature, neutralized with 1.5 M HCl and the white solid obtained is collected by vacuum filtration, washed with water and dried under vacuum to afford 4-[6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-naphthalen-2-ylmethoxy]-benzoic acid. [M]− 407.

Workup

  1. waitat 70° C. for 24 h
  2. temperatureThe reaction mixture is cooled to room temperature
  3. customthe white solid obtained
  4. filtrationis collected by vacuum filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-9bbf9f3265de41d6bc103cd7de4606aa
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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