HCID 18004193, compound → HCID 18419918, compound

HRID 990175Notes

Reaction equation

HRID 990175 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 added to 300 ml of THF under N2. At RT, dimethyl 2-(3′-(3,7-dimethyloctyloxy)phenyl)terephthalate (75.5 g, 177 mmol), dissolved in 120 ml of THF, was then slowly added dropwise. The mixture was subsequently stirred for 4 hours under reflux. After cooling, excess LiAlH4 was carefully destroyed by addition of H2O. Half-concentration H2SO4 was then carefully added dropwise (about 50 ml). The mixture became very viscous during this addition. After stirring further for 1 hour, a clear solution was obtained and a slimy gray precipitate could be seen at the bottom of the flask. The clear solution was decanted off and the solvent was taken off. The precipitate which remained was stirred with a large amount of water and ethyl acetate and, after filtration, the organic phase was separated off, the solvent was taken 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 drying over MgSO4, the solvent was taken off. The resulting oil was stirred a number of times with hexane and dried in an oil pump vacuum. The product was thus obtained as a pure pale yellow, highly viscous oil (54 g, 82%).

Workup

  1. additionwas then slowly added dropwise
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. customexcess LiAlH4 was carefully destroyed by addition of H2O
  5. concentrationHalf-concentration H2SO4
  6. additionwas then carefully added dropwise (about 50 ml)
  7. additionThe mixture became very viscous during this addition
  8. stirringAfter stirring further for 1 hour
  9. customa clear solution was obtained
  10. customThe clear solution was decanted off
  11. stirringThe precipitate which remained was stirred with a large amount of water and ethyl acetate
  12. filtrationafter filtration
  13. customthe organic phase was separated off
  14. extractionextracted five times with water
  15. dry with materialAfter drying over MgSO4
  16. stirringThe resulting oil was stirred a number of times with hexane
  17. customdried in an oil pump vacuum

Sources & evidence

ORD record
ord-c8d688ebd36f4192b930f7e4aba9d305
Source dataset
uspto-grants-2002_10
Patent number
US06458909B1

Reaction notes

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