Hydrochloric Acid → 1,3-Benzodioxole-5-carboxylic acid

HRID 252852Notes

Reaction equation

HRID 252852 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.CC(=CC)C.Cl([O-])=[O:18].[Na+].Cl>CC(O)(C)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:18])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8438PiperonalHCID 105532-Methyl-2-buteneHCID 23668197Sodium Chlorite

Product 1

HCID 71961,3-Benzodioxole-5-carboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

To a stirred solution of benzo[d][1,3]dioxole-5-carbaldehyde (254a, 2 g, 13.3 mmol), Na2H2PO4 (6.38 g, 53.2 mmol), and 2-methyl-2-butene (9.85 mL, 93.1 mmol) in t-BuOH (41 mL) and water (17 mL) was added sodium chlorite (7.19 g, 79.9 mmol). The resulting reaction mixture was stirred for 2 hours at room temperature. Water (100 mL) and 1M HCl (25 mL) were added and the mixture was extracted with EtOAc (2×50 mL). The organic phase was separated, dried with sodium sulfate and evaporated under reduced pressure. The resulting solid was triturated with EtOAc (20 mL) to yield the title compound 255a as a white solid (1.9 g, 86% yield). 1H NMR: (DMSO) δ 12.72 (br s, 1H), 7.53-7.50 (m, 1H), 7.34-7.32 (m, 1H), 6.99-6.95 (m, 1H), 6.10 (s, 2H).

Workup

  1. customThe resulting reaction mixture
  2. extractionthe mixture was extracted with EtOAc (2×50 mL)
  3. customThe organic phase was separated
  4. dry with materialdried with sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting solid was triturated with EtOAc (20 mL)

Sources & evidence

ORD record
ord-ed1f9381727f4da8b2b513fb265bea4c
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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