Formaldehyde → 3,3-Dimethyl-2-methylene-indan-1-one

HRID 495118Notes

Reaction equation

HRID 495118 reaction equation
C(N[CH2:4][CH3:5])C.OS(O)(=O)=O.[CH2:11]=O.[CH3:13][C:14]1(C)C[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:23]>>[CH3:11][C:4]1([CH3:5])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:23])[C:14]1=[CH2:13]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 8021DiethylamineHCID 3012022,2-dimethyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 686161853,3-Dimethyl-2-methylene-indan-1-oneYield 15.9%

Conditions

Temperature
110 °C

Procedure

Diethylamine (8.76 g, 0.12 mol) was cooled to 0° C. and 62.5% aq. H2SO4 was added slowly. Aqueous formaldehyde solution (36.5%, 9.86 g, 0.12 mol) was added, followed by dimethylindanone (16.0 g, 0.10 mol). The mixture was heated to 110° C. for 5.5 h. Aqueous workup yielded a ca. 1:1 mixture of starting material and product which was separated by FC on SiO2 to yield the product as a colourless oil (2.73 g, 13%).

Workup

  1. customAqueous workup yielded
  2. additiona ca. 1:1 mixture of starting material and product which
  3. customwas separated by FC on SiO2

Sources & evidence

ORD record
ord-7dcb54eaf9724e129d27e1c0e1ceddf5
Source dataset
uspto-grants-2009_05
Patent number
US07538243B2

Reaction notes

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