Water → HCID 18419923, compound

HRID 988939Notes

Reaction equation

HRID 988939 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][CH:8]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:28]=[C:27]([C:29](OCC)=[O:30])[C:26]([O:34][CH3:35])=[CH:25][C:19]=2[C:20](OCC)=[O:21])=[CH:14][CH:13]=1.O.[OH-].[Na+]>C1COCC1>[OH:21][CH2:20][C:19]1[CH:25]=[C:26]([O:34][CH3:35])[C:27]([CH2:29][OH:30])=[CH:28][C:18]=1[C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH:8]([CH3:7])[CH2:36][CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18004204HCID 18004204, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18419923HCID 18419923, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
67 °C

Procedure

LiAlH4 (7.9 g, 208 mmol) was initially introduced with about 250 ml of THF under an argon blanket. Diethyl 2-[4-(3,7-dimethyloctyloxy)phenyl]-5-methoxyterephthalate (72.2 g, 149 mmol) was diluted with about 60 ml of THF in a dropping funnel and slowly added dropwise. During this addition, the reaction mixture was stirred vigorously. The batch, diluted with a further 100 ml of THF, was then refluxed at 67° C. After 2 hours, it was cooled to RT. When the reduction was complete, 8 ml of water were carefully added for work-up. 8 ml of aqueous NaOH solution (15% strength) were subsequently added, and finally 24 ml of water were added. After each addition, the mixture was stirred for about a further 15 minutes (“1:1:3 method”). The solid formed was filtered off with suction and again stirred with THF, and finally the combined organic phases were evaporated. Recrystallization from hexane/ethyl acetate (20:1) gave the product (93% yield) as colorless crystals.

Workup

  1. additionslowly added dropwise
  2. additionDuring this addition
  3. temperatureit was cooled to RT
  4. additionAfter each addition
  5. stirringthe mixture was stirred for about a further 15 minutes (“1:1:3 method”)
  6. customThe solid formed
  7. filtrationwas filtered off with suction
  8. stirringagain stirred with THF
  9. customfinally the combined organic phases were evaporated
  10. customRecrystallization from hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-870e6ba4a0b7401691df738d3e4f466a
Source dataset
uspto-grants-2003_10
Patent number
US06638646B2

Reaction notes

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