Sodium Hydroxide → HCID 54294841, compound

HRID 2165181Notes

Reaction equation

HRID 2165181 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[H-].[H-].COCCO[Al+]OCCOC.[Na+].C[O:28][C:29](=O)[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH:38]=[C:39]([CH2:41][CH2:42][CH:43]=[C:44]([CH2:46][CH2:47][CH:48]=[C:49]([CH3:51])[CH3:50])[CH3:45])[CH3:40])=[CH:32][CH:31]=1.[OH-].[Na+].[H][H]>C1(C)C=CC=CC=1.CC(O)C.O>[CH2:37]([O:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][OH:28])=[CH:35][CH:34]=1)[CH:38]=[C:39]([CH2:41][CH2:42][CH:43]=[C:44]([CH2:46][CH2:47][CH:48]=[C:49]([CH3:51])[CH3:50])[CH3:45])[CH3:40]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 16684438Red-AlHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 53799950HCID 53799950, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54294841HCID 54294841, compound

Reagents, catalysts & solvents 3

HCID 3776IsopropanolCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4 g (14 mmol) Vitride®, which is 70% sodium bis-(2-methoxy-ethoxy)-aluminum dihydride, were added dropwise with stirring and cooling with ice at 5° to 15° C. to a solution of 5 g (14 mmol) 4-farnesyloxybenzoic acid methyl ester in 30 ml toluene. The mixture was then heated for 2 hours to the boiling temperature, cooled and 10% sodium hydroxide solution added dropwise while cooling with ice (until the evolution of hydrogen stopped). After approx. 10 ml water and a few drops 2-propanol had been added, the toluene phase was separated off, the aqueous phase was washed twice with toluene and, after drying with sodium sulfate, was concentrated by evaporation. The residue was chromatographed on silica gel (Merck) (eluent: methylene chloride/methanol 99:1). 4-farnesyloxybenzyl alcohol having a refractive index n20 of 1.5305 was obtained in a yield of 3.6 g (78% of the theoretical).

Workup

  1. additionwere added dropwise
  2. temperatureThe mixture was then heated for 2 hours to the boiling temperature
  3. temperaturecooled
  4. customthe toluene phase was separated off
  5. washthe aqueous phase was washed twice with toluene
  6. dry with materialafter drying with sodium sulfate
  7. concentrationwas concentrated by evaporation
  8. customThe residue was chromatographed on silica gel (Merck) (eluent: methylene chloride/methanol 99:1)

Sources & evidence

ORD record
ord-0aedd5f44bfa4495ab3d3d07612547fb
Source dataset
uspto-grants-1990_07
Patent number
US04939171

Reaction notes

Loading…