Lithium Hydroxide → HCID 59760044, compound

HRID 1879132Notes

Reaction equation

HRID 1879132 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([CH3:23])=[C:16]([CH:22]=2)[C:17]([O:19]CC)=[O:18])[CH:7]=[CH:8][CH:9]=1>O1CCOCC1.O>[Cl:3][C:4]1[CH:5]=[C:6]([CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([CH3:23])=[C:16]([CH:22]=2)[C:17]([OH:19])=[O:18])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59760041HCID 59760041, compound

Product 1

HCID 59760044HCID 59760044, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

Lithium hydroxide (16.3 g, 389 mmol) was added to a solution of ethyl 5-{[(3-chlorophenyl)methyl]oxy}-2-methylbenzoate (79 g, 259 mmol) in 1,4-dioxane (1 L) and water (0.5 L). The reaction mixture was stirred at 65° C. for 5 hours, allowed to cool and stood at room temperature for 14 hours. The reaction was concentrated to remove the 1,4-dioxane, and the resulting brown aqueous solution was washed with diethyl ether (3×1 L). The aqueous layer was then acidified with 2N HCl (approximately 200 ml) and the resulting precipitate filtered and washed with water to give a yellow solid. This was dried overnight at 40° C. in a vacuum oven to give the title compound as a yellow solid (66.38 g). MS (ES−) [C15H1335ClO3—H]− 275. 1H-NMR (400 MHz, d6-DMSO) δ 2.43 (3H, s), 5.14 (2H, s), 7.10-7.13 (1H, m), 7.21-7.23 (1H, m), 7.38-7.47 (4H, m), 7.52 (1H, s).

Workup

  1. temperatureto cool
  2. waitstood at room temperature for 14 hours
  3. concentrationThe reaction was concentrated
  4. customto remove the 1,4-dioxane
  5. washthe resulting brown aqueous solution was washed with diethyl ether (3×1 L)
  6. filtrationthe resulting precipitate filtered
  7. washwashed with water
  8. customto give a yellow solid
  9. customThis was dried overnight at 40° C. in a vacuum oven

Sources & evidence

ORD record
ord-e59787f314bb4c97b118a132a26717ca
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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