HCID 18004193, compound → HCID 18419918, compound

HRID 1635758Notes

Reaction equation

HRID 1635758 reaction equation
[CH3:1][CH:2]([CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:21]=[C:20]([C:22](OC)=[O:23])[CH:19]=[CH:18][C:13]=2[C:14](OC)=[O:15])[CH:9]=[CH:10][CH:11]=1>C1COCC1>[OH:15][CH2:14][C:13]1[CH:18]=[CH:19][C:20]([CH2:22][OH:23])=[CH:21][C:12]=1[C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][CH2:3][CH:2]([CH3:1])[CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH:7]=1

Participants

3

Reactant 1

HCID 18004193HCID 18004193, compound

Product 1

HCID 18419918HCID 18419918, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiAH4 (9.4 g, 248 mmol) and 300 ml of THF were placed in a reaction vessel under N2. At RT, dimethyl 2-(3′-(3,7-dimethyl-octyloxy)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-concentrated H2SO4 (about 50 ml) was then carefully added dropwise. The mixture became very viscous during this addition. After stirring further for 1 hour, a clear solution and, at the bottom of the flask, a slimy gray precipitate could be seen. The clear solution was decanted off and the solvent was taken off. The precipitate which remained was stirred with plenty of water and ethyl acetate, the organic phase was separated off after filtration, 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 obtained as a pure, light 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. additionHalf-concentrated H2SO4 (about 50 ml) was then carefully added dropwise
  6. additionThe mixture became very viscous during this addition
  7. stirringAfter stirring further for 1 hour
  8. customThe clear solution was decanted off
  9. stirringThe precipitate which remained was stirred with plenty of water and ethyl acetate
  10. customthe organic phase was separated off
  11. filtrationafter filtration
  12. extractionextracted five times with water
  13. dry with materialAfter drying over MgSO4
  14. stirringThe resulting oil was stirred a number of times with hexane
  15. customdried in an oil pump vacuum

Sources & evidence

ORD record
ord-867c1460b7a34342a5cec1e023cd8b99
Source dataset
uspto-grants-2003_01
Patent number
US06509507B2

Reaction notes

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