Lithium Hydroxide → 8-Methyl-2,3-dihydro-1,4-benzodioxine-6-carboxylic acid

HRID 642836Notes

Reaction equation

HRID 642836 reaction equation
[Li+].[OH-].[CH3:3][C:4]1[C:9]2[O:10][CH2:11][CH2:12][O:13][C:8]=2[CH:7]=[C:6]([C:14]([O:16]C)=[O:15])[CH:5]=1.[OH-].[Na+]>O.C1COCC1>[CH3:3][C:4]1[C:9]2[O:10][CH2:11][CH2:12][O:13][C:8]=2[CH:7]=[C:6]([C:14]([OH:16])=[O:15])[CH:5]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 45122025Methyl 8-methyl-2,3-dihydro-1,4-benzodioxin-6-carboxylate

Product 1

HCID 451220248-Methyl-2,3-dihydro-1,4-benzodioxine-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.65 g (0.28 mol) LiOH in 100 mL water was metered into a solution of 33.60 g (0.16 mol) methyl 8-methyl-2,3-dihydro-1,4-benzodioxin-6-carboxylate in 200 mL THF and the reaction solution was stirred overnight at RT. To complete the reaction 150 mL 6 M NaOH were added and the mixture was stirred for a further 2 h at 50° C. The reaction mixture was evaporated down i.vac, the residue was combined with THF, acidified with conc. HCl while cooling with ice, the precipitate was filtered off, washed with 150 mL water and dried at 60° C. in the circulating air dryer.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for a further 2 h at 50° C
  3. customThe reaction mixture was evaporated down i.vac
  4. temperaturewhile cooling with ice
  5. filtrationthe precipitate was filtered off
  6. washwashed with 150 mL water
  7. customdried at 60° C. in the circulating air dryer

Sources & evidence

ORD record
ord-5b61e9b4be5a420c8cd3368b8cc611f6
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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