Hydrochloric Acid → Benzeneundecanol

HRID 1703074Notes

Reaction equation

HRID 1703074 reaction equation
B.[C:2]1([CH:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])C(O)=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[O:22]1CCC[CH2:23]1>O>[C:2]1([CH2:8][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:23][OH:22])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 8028Tetrahydrofuran2×HCID 211154592-Phenylundecanoic acid

Product 1

HCID 11651716Benzeneundecanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 200 ml. of 1 M borane in tetrahydrofuran, cooled in an ice bath under nitrogen, is added dropwise over 35 minutes, a solution of 52.5 g. of phenylundecanoic acid in 150 ml. of tetrahydrofuran. The solution is allowed to stand at room temperature for 5.5 hours and poured onto ice. To the mixture is added 8 ml. of concentrated hydrochloric acid and the mixture is diluted with water to 2.2 liters. The mixture is extracted with ether (ca 500 ml.) and the extracts dried over magnesium sulfate. Concentration in vacuo gives a colorless oil.

Workup

  1. additionis added dropwise over 35 minutes
  2. additionpoured onto ice
  3. additionTo the mixture is added 8 ml
  4. extractionThe mixture is extracted with ether (ca 500 ml.)
  5. dry with materialthe extracts dried over magnesium sulfate
  6. concentrationConcentration in vacuo
  7. customgives a colorless oil

Sources & evidence

ORD record
ord-1c15409f64484bbdb12da75dc9d6b47b
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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