Hydrochloric Acid → 2,4,6-trimethyl-1H-indene

HRID 1459021Notes

Reaction equation

HRID 1459021 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([CH3:12])[CH:6]=[C:7]([CH3:11])[CH:8]=2)[C:3]1=O.[BH4-].[Na+].Cl>O1CCCC1.CO>[CH3:1][C:2]1[CH2:10][C:9]2[C:4]([CH:3]=1)=[C:5]([CH3:12])[CH:6]=[C:7]([CH3:11])[CH:8]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 117690492,5,7-Trimethyl-1-indanone

Product 1

HCID 109207862,4,6-trimethyl-1H-indeneYield 96%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

20.4 g (117 mmol) of 2,5,7-trimethyl-1-indanone (1) were dissolved in 300 ml of a mixture of tetrahydrofuran/methanol (2:1), and 6.6 g (175 mmol) of NaBH4 were added at room temperature. The mixture was stirred for a further hour, 50 ml of half-concentrated HCl were added and the mixture was extracted with ether. The combined organic phases were dried over sodium sulfate and freed from the solvent. The residue was transferred to a distillation apparatus, and 13 g of magnesium sulfate were added. A vacuum of about 10 mbar was applied and the mixture was heated up until the product distilled over (130°-150° C.). Distillation gave 17.7 g of the indene 2 as a colorless oil. The yield was 96%.

Workup

  1. additionwere added at room temperature
  2. extractionthe mixture was extracted with ether
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. additionwere added
  5. temperaturethe mixture was heated up until the product
  6. distillationdistilled over (130°-150° C.)
  7. distillationDistillation

Sources & evidence

ORD record
ord-f10032f0c6fd4509b43a4e64531c36cd
Source dataset
uspto-grants-1998_12
Patent number
US05852142

Reaction notes

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