Hydrochloric Acid → (4-Decylphenyl)methanol

HRID 1703111Notes

Reaction equation

HRID 1703111 reaction equation
B.[CH2:2]([C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].Cl>O1CCCC1>[CH2:2]([C:12]1[CH:13]=[CH:14][C:15]([CH2:16][OH:17])=[CH:19][CH:20]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 123614764-Decylbenzoic acid

Product 1

HCID 13079698(4-Decylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 69.5 ml. of 1 molar borane in tetrahydrofuran chilled in an ice bath is added dropwise over 40 minutes a solution of 17.2 g. of p-decylbenzoic acid in 150 ml. of dry tetrahydrofuran. The mixture is refluxed for 3.5 hours, chilled, 5 ml. of concentrated hydrochloric acid is added and the mixture poured onto ice. The mixture is filtered and the solid washed with water to give white crystals.

Workup

  1. additionis added dropwise over 40 minutes a solution of 17.2 g
  2. temperatureThe mixture is refluxed for 3.5 hours
  3. temperaturechilled
  4. additionthe mixture poured onto ice
  5. filtrationThe mixture is filtered
  6. washthe solid washed with water
  7. customto give white crystals

Sources & evidence

ORD record
ord-76f58722c44044cf98d0d5129f6d3350
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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