Sodium Hydroxide → HCID 57321997, compound

HRID 1395215Notes

Reaction equation

HRID 1395215 reaction equation
C([O:3][C:4](=O)[C:5]([CH3:19])=[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH2:17][CH3:18])([CH3:16])[CH3:15])=[CH:10][CH:9]=1)[CH3:7])C.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:14]([C:11]1[CH:10]=[CH:9][C:8]([C:6]([CH3:7])=[C:5]([CH3:19])[CH2:4][OH:3])=[CH:13][CH:12]=1)([CH2:17][CH3:18])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57324578HCID 57324578, compound

Product 1

HCID 57321997HCID 57321997, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-10 °C

Procedure

110 G. of a 70% sodium dihydro-bis-(2-methoxyethoxy)-aluminate solution in toluene are added dropwise at 25°-30° C. over a period of 90 minutes to a solution of 85 g. of 3-(p-tert.-amyl-phenyl)-2,3-dimethyl-acrylic acid ethyl ester in 400 ml. of absolute toluene and the mixture is subsequently warmed at 40° C. for 2 hours. The mixture is then cooled down to -10° C. and treated dropwise over 300 ml. of 2 N sodium hydroxide. The toluene phase is separated and the aqueous-alkaline phase is back-extracted twice with 300 ml. of toluene. The combined toluene phases are washed neutral with water, dried over sodium sulfate and evaporated. By distillation there is obtained pure 3-(p-tert.-amyl-phenyl)-2,3-dimethyl-allyl alcohol; nD20 =1.5311.

Workup

  1. additiontreated dropwise over 300 ml
  2. customThe toluene phase is separated
  3. extractionthe aqueous-alkaline phase is back-extracted twice with 300 ml
  4. washThe combined toluene phases are washed neutral with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. distillationBy distillation there

Sources & evidence

ORD record
ord-69d8ab2b328f49c1b2c1d2767402801a
Source dataset
uspto-grants-1980_05
Patent number
US04202894

Reaction notes

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