Sulfuric Acid → (4-Propylphenyl)methanol

HRID 597769Notes

Reaction equation

HRID 597769 reaction equation
[BH4-].[Na+].S(=O)(=O)(O)O.[CH2:8]([C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=1)[CH2:9][CH3:10].[OH-].[Na+]>CCOCC.O1CCCC1.CO>[CH2:8]([C:11]1[CH:19]=[CH:18][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 1376014-Propylbenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 2760472(4-Propylphenyl)methanolYield 90.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of sodium borohydride (2.9 g, 76 mmol) and concentrated sulfuric acid in ether (prepared by adding 2.0 ml of concentrated sulfuric acid to 4.0 ml of ether) was added dropwise to a solution of p-n-propylbenzoic acid (5.0 g, 32 mmol) in tetrahydrofuran (20 ml) cooled to 0° C. keeping the temperature of the reaction system below 20° C., and then this mixture was stirred at room temperature for 3 hours. After the mixture was cooled on ice, methanol and 1 N sodium hydroxide were added, and this mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give the title compound (4.33 g). This compound was used in the following reaction without purification.

Workup

  1. customthe temperature of the reaction system below 20° C.
  2. additionwere added
  3. extractionthis mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d0dd117975bb4f1fa1b0064a511fcf44
Source dataset
uspto-grants-2011_03
Patent number
US07897387B2

Reaction notes

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