3,4-Dihydroxybenzaldehyde → Dilinoleylbenzaldehyde

HRID 638771Notes

Reaction equation

HRID 638771 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1O)[CH:5]=O.[C:11](=[O:14])([O-])[O-].[Cs+].[Cs+].S(O[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])(=O)(=O)C>COCCOCCOC>[CH2:5]([C:4]1[C:3]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[C:2]([CH:9]=[CH:8][CH:7]=1)[CH:11]=[O:14])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

5

Reactant 3

HCID 87683,4-DihydroxybenzaldehydeHCID 10796Cesium carbonateHCID 59753235Linoleyl methanesulfonate

Product 1

HCID 86608586DilinoleylbenzaldehydeYield 98.7%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
100 °C

Procedure

3,4-Dihydroxybenzaldehyde (2.76 g, 20.0 mmol) was weighed into a 200 mL round bottomed flask with a stir bar. The flask was charged with diglyme (100 mL), septum sealed and flushed with argon. Cesium carbonate (19.5 g, 60.0 mmol) was added to the solution slowly in portions. Linoleyl mesylate (15.2 g, 44.0 mmol) was added via syringe. The reaction mixture was heated to 100° C. under slight positive pressure of argon. The reaction mixture was cooled to room temperature and filtered. The solids were washed with 1,2-dichloroethane. The combined filtrate and washes were concentrated and then dried under high vacuum at 65° C. to remove residual diglyme. The resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes) to afford 11.9 g (94%) of a brown oil.

Workup

  1. customsealed
  2. customflushed with argon
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. washThe solids were washed with 1,2-dichloroethane
  6. concentrationThe combined filtrate and washes were concentrated
  7. customdried under high vacuum at 65° C.
  8. customto remove residual diglyme
  9. customThe resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d8e9f96e586443b7bc5a64069ecb63f1
Source dataset
uspto-grants-2010_04
Patent number
US07691405B2

Reaction notes

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