HCID 18004193, compound → HCID 18419918, compound

HRID 988941Notes

Reaction equation

HRID 988941 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][CH:8]([CH2:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:27]=[C:26]([C:28](OC)=[O:29])[CH:25]=[CH:24][C:19]=2[C:20](OC)=[O:21])[CH:15]=[CH:16][CH:17]=1>C1COCC1>[OH:21][CH2:20][C:19]1[CH:24]=[CH:25][C:26]([CH2:28][OH:29])=[CH:27][C:18]=1[C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][CH2:9][CH:8]([CH3:7])[CH2:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH:13]=1

Participants

4

Reactant 2

HCID 18004193HCID 18004193, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18419918HCID 18419918, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiAlH4 (9.4 g, 248 mmol) was initially introduced in 300 ml of THF under N2. Dimethyl 2-(3′-(3,7-dimethyloctyloxy)phenyl)terephthalate (75.5 g, 177 mmol), dissolved in 120 ml of THF, was then slowly added dropwise at RT. The mixture was subsequently stirred under reflux for 4 hours and cooled. Excess LiAlH4 was then carefully destroyed by addition of H2O. Semiconcentrated H2SO4 was subsequently carefully added dropwise (about 50 ml). The batch was of very low viscosity at this point. After a subsequent stirring time of 1 hour, a clear solution and a gray precipitate at the bottom of the flask were observed. The clear solution was decanted off, and the solvent was stripped off. The precipitate which remained was stirred with plenty of water and ethyl acetate and filtered, the organic phase was separated off, the solvent was stripped off, and combined with the first organic phase. The combined organic phases were taken up in ethyl acetate and extracted five times with water. After the extracts had been dried over MgSO4, the solvent was stripped off. The resultant oil was stirred a number of times with hexane and dried in an oil-pump vacuum, giving the product as a pure, pale-yellow, high-viscosity oil (54 g, 82%).

Workup

  1. additionwas then slowly added dropwise at RT
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. customExcess LiAlH4 was then carefully destroyed by addition of H2O
  5. additionSemiconcentrated H2SO4 was subsequently carefully added dropwise (about 50 ml)
  6. customAfter a subsequent stirring time of 1 hour
  7. customThe clear solution was decanted off
  8. stirringThe precipitate which remained was stirred with plenty of water and ethyl acetate
  9. filtrationfiltered
  10. customthe organic phase was separated off
  11. extractionextracted five times with water
  12. dry with materialAfter the extracts had been dried over MgSO4
  13. stirringThe resultant oil was stirred a number of times with hexane
  14. customdried in an oil-pump vacuum

Sources & evidence

ORD record
ord-7d6864fa8e17443a86974e2fd0565b53
Source dataset
uspto-grants-2003_10
Patent number
US06638646B2

Reaction notes

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