Bromoacetic Acid → HCID 23132008, compound

HRID 2424265Notes

Reaction equation

HRID 2424265 reaction equation
[CH3:1][C:2]1([CH3:15])[CH:8]2[CH:9]3[CH2:12][CH2:13][CH:7]2[C:6]([CH3:14])([C:10]3=C)[CH2:5][CH2:4][CH2:3]1.Br[CH2:17]C(O)=O>>[CH:2]([C:8]12[CH2:10][C:6]3([CH3:14])[C:7]([CH3:17])([CH2:13][CH2:12][CH2:9]1)[CH:3]2[CH2:4][CH2:5]3)([CH3:1])[CH3:15]

Participants

3

Procedure

In a 2 L four-necked flask, 1,000 g of longifolene (manufactured by Yasuhara Chemical Co., Ltd.) and 100 g of bromoacetic acid were placed and reacted at 170° C. for 18 hours. The reaction mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and with water and then refined by distillation. Thereafter, the refined product was placed in a 2 L autoclave together with 18 g of a palladium-carbon hydrogenation catalyst and subjected to hydrogenation (hydrogen pressure: 6 MPa, reaction temperature: 100° C., reaction time: 2 hours). After completion of the reaction, the catalyst was removed by filtration. The filtrate was subjected to fractional distillation to obtain 200 g of the desired 4-isopropyl-1,7a-dimethyl-octahydro-1,4-methano-indene (Fluid 3). The results of the measurements of the properties and the traction coefficient are shown in Table 1.

Workup

  1. customreacted at 170° C. for 18 hours
  2. washThe reaction mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and with water
  3. distillationrefined by distillation
  4. customsubjected to hydrogenation (hydrogen pressure: 6 MPa, reaction temperature: 100° C., reaction time: 2 hours)
  5. customAfter completion of the reaction
  6. customthe catalyst was removed by filtration
  7. distillationThe filtrate was subjected to fractional distillation

Sources & evidence

ORD record
ord-8cd2a16beb8945f4b223639c73c0728a
Source dataset
uspto-grants-2011_06
Patent number
US07964540B2

Reaction notes

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