Potassium Hydroxide → HCID 13102419, compound

HRID 648222Notes

Reaction equation

HRID 648222 reaction equation
[OH:1][CH2:2][C:3]1([CH3:12])[CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4]1.[OH-].[K+].[Mn]([O-])(=O)(=O)=[O:16].[K+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O>[CH3:12][C:3]1([C:2]([OH:16])=[O:1])[CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4]1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 656671Sodium PyrosulfiteHCID 20482667(2-Methyl-2,3-dihydro-1-benzofuran-2-yl)methanol

Product 1

HCID 13102419HCID 13102419, compoundYield 16.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The 2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran (16.4 g) and potassium hydroxide (5.2 g) in water (150 ml) were mixed and cooled to 5°. Potassium permanganate (20 g) was added portionwise over 45 minutes to the stirred mixture maintained below 12°. After the addition was complete stirring was continued for 1 hour and the mixture was then diluted with water. Sodium metabisulphite was added to destroy the precipitated MnO2 followed by an excess of sodium carbonate. The basic aqueous phase was washed with methylene chloride and then acidified with 2 N hydrochloric acid. Extraction with methylene chloride followed by washing, drying and evaporation of the extracts gave the carboxylic acid (3.0 g); I.R. νmax 1720 cm-1.

Workup

  1. temperaturecooled to 5°
  2. temperaturemaintained below 12°
  3. additionAfter the addition
  4. customto destroy the precipitated MnO2
  5. washThe basic aqueous phase was washed with methylene chloride
  6. extractionExtraction with methylene chloride
  7. washby washing
  8. customdrying
  9. customevaporation of the extracts

Sources & evidence

ORD record
ord-34a7a48af6a24a33a7a87794fd28379d
Source dataset
uspto-grants-1983_10
Patent number
US04411908

Reaction notes

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