Hydrochloric Acid → 4-Decyloxybenzyl alcohol

HRID 1703073Notes

Reaction equation

HRID 1703073 reaction equation
B.[CH2:2]([O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].Cl>O1CCCC1.O>[CH2:2]([O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][OH:18])=[CH:20][CH:21]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 1385274-(Decyloxy)benzoic acid

Product 1

HCID 130796524-Decyloxybenzyl alcohol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 100 ml. of 1.0 M borane in tetrahydrofuran cooled in an ice bath under nitrogen is added dropwise, 27.8 g. of p-decyloxybenzoic acid in 300 ml. of tetrahydrofuran over a period of 45 minutes. The mixture is stirred at room temperature for 6 hours and poured onto ice, diluted with water and 10 ml. of concentrated hydrochloric acid. The mixture is filtered and the solid washed with water to give white crystals. Recrystallization from ethanol gives white plates, m.p. 57.5°-59° C.

Workup

  1. additionis added dropwise
  2. additionpoured onto ice
  3. filtrationThe mixture is filtered
  4. washthe solid washed with water
  5. customto give white crystals
  6. customRecrystallization from ethanol
  7. customgives white plates, m.p. 57.5°-59° C.

Sources & evidence

ORD record
ord-1886cca7e74b47babd18d00a53db5053
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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