4-(4-Methoxyphenyl)butyric acid → 4-(4-Methoxyphenyl)butan-1-ol

HRID 2057653Notes

Reaction equation

HRID 2057653 reaction equation
B#B.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][C:14](O)=[O:15])=[CH:7][CH:6]=1>O1CCCC1>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 782804-(4-Methoxyphenyl)butyric acidHCID 6328200Diboron

Product 1

HCID 976604-(4-Methoxyphenyl)butan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A flask containing 250 ml. 1 M diborane in tetrahydrofuran is thoroughly cooled in an ice-water bath. To the stirred solution is slowly added 38.8 g. of 4-(4-methoxyphenyl)butyric cid in 100 ml. tetrahydrofuran. After addition is completed the reaction is stirred for 16 hours at room temperature, then poured slowly into 1 l. stirred ice-water. The aqueous solution is extracted three times with 300 ml. portions of ether. The combined organic extracts are washed with water and brine, dried, and evaporated to a nearly colorless oil of 4-(4-methylphenyl)-1-butanol.

Workup

  1. additionA flask containing 250 ml
  2. additionAfter addition
  3. additionpoured slowly into 1 l
  4. extractionThe aqueous solution is extracted three times with 300 ml
  5. washThe combined organic extracts are washed with water and brine
  6. customdried
  7. customevaporated to a nearly colorless oil of 4-(4-methylphenyl)-1-butanol

Sources & evidence

ORD record
ord-89b7039924734203883ea63dbddb346b
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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