Hydrochloric Acid → 959749-03-2

HRID 1466638Notes

Reaction equation

HRID 1466638 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH:13]2[CH2:15][CH2:14]2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH:13]2[CH2:14][CH2:15]2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66846877959749-02-1

Product 1

HCID 66846845959749-03-2Yield 96%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
60 °C

Procedure

Methyl 5-chloro-2-cyclopropoxybenzoate was dissolved in THF/H2O (1:1, 400 mL), then sodium hydroxide (16 g, 0.4 mol) was added. The mixture was heated to 60° C. and stirred for 1 hour. The reaction mixture was cooled to room temperature, then the pH was adjusted to 4 using 4N aqueous HCl, resulting in precipitation of the product. The precipitate was collected by filtration and azeotroped with toluene to afford 19 g (96%) of 5-chloro-2-cyclopropoxybenzoic acid. 1H NMR (400 MHz, CDCl3) δ: 12.96 (br, 1H), 7.58 (m, 2H), 7.43 (q, 1H), 3.91 (m, 1H), 0.81 (m, 4H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customresulting in precipitation of the product
  3. filtrationThe precipitate was collected by filtration
  4. customazeotroped with toluene

Sources & evidence

ORD record
ord-563c5a94eb3a4ebea57dc362ec2bdb77
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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