Hydrochloric Acid → 4-Heptyloxybenzyl alcohol

HRID 979419Notes

Reaction equation

HRID 979419 reaction equation
B.[Na].[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].Cl.O>C(O)(C)C>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][OH:16])=[CH:17][CH:18]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 119740Benzaldehyde, 4-(heptyloxy)-HCID 178418435HCID 178418435, compound

Product 1

HCID 130796974-Heptyloxybenzyl alcoholYield 62.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
70 °C

Procedure

A suspension of sodium boron hydride (6.9 g) in isopropyl alcohol (500 ml) was dropwise added to a solution of p-heptyloxybenzaldehyde (119 g) in isopropyl alcohol (300 ml), followed by heating the mixture to 70° C. to form a uniform solution, which was then agitated at 70° C. for 3 hours and allowed to stand overnight, followed by adding 6N-HCl (100 ml) and water (200 ml), heating the mixture to 60° C., distilling off most of the solvent, extracting with toluene, washing with water, washing with alkali, washing with water to make it neutral, drying, concentrating and recrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml) to obtain p-heptyloxybenzyl alcohol (74.9 g). This product (40 g) together with 47% aqueous hydrogen bromic acid (200 g) were agitated at 80° C. for 7 hours and allowed to stand overnight, followed by extracting with n-heptane (200 ml), washing the n-heptane layer with water till the washing water became neutral, drying, concentrating and subjecting the residue to vacuum distillation to obtain p-heptyloxybenzyl bromide (IIa-2) (28 g) having a b.p. of 174°-175° C./6 Torr.

Workup

  1. customto form a uniform solution, which
  2. waitto stand overnight
  3. temperatureheating the mixture to 60° C.
  4. distillationdistilling off most of the solvent
  5. extractionextracting with toluene
  6. washwashing with water
  7. washwashing with alkali,
  8. washwashing with water
  9. customdrying
  10. concentrationconcentrating
  11. customrecrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml)

Sources & evidence

ORD record
ord-6b7e927a0c9443e5af0eaef8e7b98efb
Source dataset
uspto-grants-1987_05
Patent number
US04668427

Reaction notes

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