Potassium Sodium Tartrate → HCID 69836284, compound

HRID 2268110Notes

Reaction equation

HRID 2268110 reaction equation
C([O:3][C:4](=O)/[CH:5]=[C:6](/[C:8]1[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:11]=[C:10]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:9]=1[O:22][CH2:23][CH2:24][CH2:25][CH3:26])\[CH3:7])C.[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>CCOCC>[C:18]([C:10]1[C:9]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:8]([CH:6]([CH3:7])/[CH:5]=[CH:4]\[OH:3])[CH:13]=[C:12]([C:14]([CH3:15])([CH3:16])[CH3:17])[CH:11]=1)([CH3:19])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 69836846HCID 69836846, compound

Product 1

HCID 69836284HCID 69836284, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

0.9 g of (E)-3-(3,5-di-tert.-butyl-2-butyloxyphenyl)-butenoic acid ethyl ester was dissolved in 20 ml of dry ether. This was cooled to −78° C. and treated with 6.0 ml of diisobutylaluminum hydride (1.0M in hexane). The temperature was allowed to warm to 0° C. and was then treated with 20% aqueous Rochelle salt. This was stirred at 25° C. for 1 hr. The organic fraction was separated, washed with water, dried (Na2SO4), and had solvent removed to give 0.78 g of (Z)-3-(3,5-di-tert.-butyl-2-butyloxyphenyl)-buten-1-ol. 1H NMR (CDCl3) δ 7.08 (dd, 4H, aromatics), 5.90 (t, 1H, CH—OH), 3.80 (t, 2H, —OCH2—), 2.49 (t, 1H, —OH), 2.21 (s, 3H).

Workup

  1. temperatureto warm to 0° C.
  2. customThe organic fraction was separated
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. customremoved

Sources & evidence

ORD record
ord-c1022b1a7b5842f2a3612b4fc6ab2fbe
Source dataset
uspto-grants-2001_12
Patent number
US06326397B1

Reaction notes

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