Acetic Acid → HCID 131716584, compound

HRID 1032633Notes

Reaction equation

HRID 1032633 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][OH:12])[CH2:3]1.CC1C(C)=NC=CC=1.[C:22](O)(=[O:24])[CH3:23]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][O:12][C:22](=[O:24])[CH3:23])[CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 114202,3-LutidineHCID 15105986HCID 15105986, compound

Product 1

HCID 131716584HCID 131716584, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

To a mixture of 12.3 g (70 mmol) of 1,1-dimethyl-3hydroxymethylindane (IX), 12.8 g of dimethylpyridine, and 20 ml of toluene, 8.6 g (84 mmol) of acetic acid was added dropwise over 10 minutes at room temperature. After the addition, the mixture was stirred for 5 hours at 30° C. to complete the reaction. After extraction with ether and removal of dimethylpyridine with 10% sulfuric acid, the residue was dried over anhydrous magnesium sulfate. The solvent was removed from the organic layer and the residue was distilled under reduced pressure to produce 11.6 g (53 mmol) of (1,1-dimethylindane-3-yl)methylacetate at a yield of 76%. The product was a colorless, transparent liquid having a woody, floral odor with a weak fruity sensation.

Workup

  1. additionwas added dropwise over 10 minutes at room temperature
  2. additionAfter the addition
  3. customthe reaction
  4. extractionAfter extraction
  5. customwith ether and removal of dimethylpyridine with 10% sulfuric acid
  6. dry with materialthe residue was dried over anhydrous magnesium sulfate
  7. customThe solvent was removed from the organic layer
  8. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-91ba0dea0035432091116c366d236d16
Source dataset
uspto-grants-1990_09
Patent number
US04959349

Reaction notes

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