Hydrochloric Acid → 4-(4-Methoxybenzyl)benzyl alcohol

HRID 262197

Reaction equation

HRID 262197 reaction equation
B.[CH3:2][O:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.Cl>O1CCCC1>[CH3:2][O:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C:9]2[CH:17]=[CH:16][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 2579874-(4-Methoxybenzyl)benzoic acid

Product 1

HCID 2584334-(4-Methoxybenzyl)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 110 ml. (0.11 m) of 1M boron hydride (BH3) in tetrahydrofuran was slowly added to a solution of 24.2 g. (0.10 m) of 4-(4-methoxybenzyl)benzoic acid in 110 ml. of tetrahydrofuran at 0° C. The addition was complete in 20 minutes and the reaction mixture was stirred at room temperature for one hour. The reaction mixture was carefully acidified with hydrochloric acid and the solvent removed. The residue was partitioned between water and ether, and the ether layer was washed with aqueous sodium hydroxide, dried over anhydrous magnesium sulfate and concentrated to give 22.2 g. of 4-(4-methoxybenzyl)benzyl alcohol, m.p. 68°-72° C. when recrystallized from cyclohexane.

Workup

  1. customat 0° C
  2. additionThe addition
  3. customthe solvent removed
  4. customThe residue was partitioned between water and ether
  5. washthe ether layer was washed with aqueous sodium hydroxide
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give 22.2 g
  9. customof 4-(4-methoxybenzyl)benzyl alcohol, m.p. 68°-72° C. when recrystallized from cyclohexane

Sources & evidence

ORD record
ord-9128d8cd9a484568836760dd80bcfde5
Source dataset
uspto-grants-1979_05
Patent number
US04153719

Linked notes

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