4-Hydroxybenzyl Alcohol → HCID 14573506, compound

HRID 2073635Notes

Reaction equation

HRID 2073635 reaction equation
[CH:1]1[C:6]([CH2:7][OH:8])=[CH:5][CH:4]=[C:3]([OH:9])[CH:2]=1.C1(C)C=CC(S(O[CH2:20][CH2:21][CH:22]([C:27]([F:30])([F:29])[F:28])[CH2:23][CH2:24][CH2:25][CH3:26])(=O)=O)=CC=1.[OH-].[Na+].Cl>C(O)C>[F:28][C:27]([F:29])([F:30])[CH:22]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:21][CH2:20][O:9][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][OH:8])=[CH:1][CH:2]=1

Participants

6

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14533171HCID 14533171, compound

Product 1

HCID 14573506HCID 14573506, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In a round-bottomed flask, a solution of 2.4 g of p-hydroxybenzyl alcohol in 10 ml of ethanol and 5.3 g of (+)-3-trifluoromethylheptyl p-toluenesulfonate were placed, and a solution of 0.8 g of sodium hydroxide in 10 ml of ethanol was added thereto dropwise, followed by 6 hours of heat-refluxing, cooling by standing and acidification with hydrochloric acid. The organic layer was extracted with diethyl ether. The resultant ether solution was dried with sodium sulfate and subjected to distilling-off of the solvent and purification by silica gel column chromatography to obtain 4.4 g of (+)-p-(3-trifluoromethylheptyloxy)benzyl alcohol. [α]D28 +1.0°, [α]43527 +2.4° (c 5.0, chloroform).

Workup

  1. temperatureof heat-refluxing
  2. temperaturecooling
  3. extractionThe organic layer was extracted with diethyl ether
  4. dry with materialThe resultant ether solution was dried with sodium sulfate
  5. distillationsubjected to distilling-off of the solvent and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-5689b4a107b640fb8ada2051e099267c
Source dataset
uspto-grants-1990_04
Patent number
US04918213

Reaction notes

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