Sodium Hydroxide → 68281-27-6

HRID 434522Notes

Reaction equation

HRID 434522 reaction equation
[OH:1][CH2:2][C:3]1([CH3:13])[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.[OH:14]C1(C)COC2C=CC=CC=2OC1.[OH-].[Na+].[Mn]([O-])(=O)(=O)=O.[K+]>O>[CH3:13][C:3]1([C:2]([OH:14])=[O:1])[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 3778286HCID 3778286, compoundHCID 126375283-Methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-ol

Product 1

HCID 1263753668281-27-6

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture (23.7 g) of 2-hydroxymethyl-2-methyl-1,4-benzodioxan and 3-hydroxy-3-methyl-2H-1,5-benzodioxepine (~3:1 ratio; prepared according to the method of A. Salimbeni, E. Manghisi, J. Heterocyclic Chem., 17, 489, 1980) was stirred with 1 N aqueous sodium hydroxide solution (135 ml) and cooled to 0°-10°. A solution of potassium permanganate (42 g) in water (165 ml) was added slowly so that the temperature was maintained below 10°. After 48 hours at room temperature the mixture was filtered and the filtrate acidified with 1 M aqueous sulphuric acid and extracted with methylene chloride. The extracts were washed with aqueous sodium bicarbonate solution and the aqueous layer was acidified with sulphuric acid. Extraction with methylene chloride followed by washing, drying and evaporation of the extracts gave the carboxylic acid (11.5 g); m.p. 125°-129.5°.

Workup

  1. customprepared
  2. temperaturecooled to 0°-10°
  3. temperaturewas maintained below 10°
  4. filtrationAfter 48 hours at room temperature the mixture was filtered
  5. extractionextracted with methylene chloride
  6. washThe extracts were washed with aqueous sodium bicarbonate solution
  7. extractionExtraction with methylene chloride
  8. washby washing
  9. customdrying
  10. customevaporation of the extracts

Sources & evidence

ORD record
ord-3d16da0dc31f47b6a489f20ce23e880c
Source dataset
uspto-grants-1983_08
Patent number
US04397860

Reaction notes

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