Hydrochloric Acid → 890927-00-1

HRID 18941Notes

Reaction equation

HRID 18941 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:11]([O:13]C)=[O:12].C1COCC1.O[Li].O.Cl>O>[Cl:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 58679275Methyl 4-chlorobenzo[d][1,3]dioxole-5-carboxylate

Product 1

HCID 58679335890927-00-1

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

To a vial containing methyl 4-chlorobenzo[d][1,3]dioxole-5-carboxylate (395.8 mg, 1.8 mmol, 1 equiv.) in 3:1 THF:H2O (15 mL) was added LiOH.H2O (153.3 mg, 3.7 mmol, 2 equiv.). The vial was capped and the mixture was stirred at 70° C. for 2 h, diluted with water, acidified with 1M HCl to pH <3, and extracted with ethyl acetate. The combined organic layers was dried over anhydrous Na2SO4, filtered and the solvent was removed under vacuum to give a quantitative yield of 4-chlorobenzo[d][1,3]dioxole-5-carboxylic acid as a white solid.

Workup

  1. customThe vial was capped
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-67dde00b9a0542329d25964fcdd35c37
Source dataset
uspto-grants-2010_06
Patent number
US07741479B2

Reaction notes

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