Hydrochloric Acid → 11-Phenyl-8-undecenol

HRID 978674Notes

Reaction equation

HRID 978674 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18]C2CCCCO2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:1]1([CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 536773642-(11-Phenyl-8-undecenyloxy)-tetrahydropyran

Product 1

HCID 5394137611-Phenyl-8-undecenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of step (b) (8.7 g) in tetrahydrofuran (150 ml) of 2M hydrochloric acid was stirred at room temperature for 4 hours. The mixture was neutralised with sodium bicarbonate solution and extracted with dichloromethane. Evaporation of the extract and chromatography of the residue on silica gel eluting with 1:1 ether:hexane to remove starting material, then with ether, gave the title product as a pale oil.

Workup

  1. extractionextracted with dichloromethane
  2. customEvaporation of the
  3. extractionextract
  4. customchromatography of the residue on silica gel eluting with 1:1 ether:hexane to remove

Sources & evidence

ORD record
ord-f72567daa6cd466790686804e0e68929
Source dataset
uspto-grants-1987_05
Patent number
US04665189

Reaction notes

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