p-Dodecyloxybenzaldehyde → 4-Dodecyloxybenzyl alcohol

HRID 631035Notes

Reaction equation

HRID 631035 reaction equation
[CH2:1]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[BH4-].[Na+]>C1COCC1>[CH2:1]([O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][OH:19])=[CH:20][CH:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 141069p-DodecyloxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 144776284-Dodecyloxybenzyl alcoholYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(dodecyloxy)-benzaldehyde (10 g, 35 mmol) in THF (80 mL) was added dropwise to a stirred suspension of NaBH4 (2.7 g, 70 mmol) in dry THF (70 mL) at 0° C. The reaction mixture was stirred at room temperature overnight and was quenched with a small amount of water (5 mL). The solid formed was removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in CHCl3 (50 mL). The resulting solution was washed with brine (3×20 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to give a white powder (9.56 g, 94%). 1H NMR (400 MHz, CDCl3, δ): 7.29 (d, J=8.4 Hz, 2H), 6.90 (d, J=8.8 Hz, 2H), 4.62 (d, J=6.0 Hz, 2H), 3.97 (t, J=6.8 Hz, 2H), 1.79-1.51 (m, 2H), 1.51-1.26 (m, 19H), 0.90 (t, J=6.4 Hz, 3H).

Workup

  1. customwas quenched with a small amount of water (5 mL)
  2. customThe solid formed
  3. customwas removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in CHCl3 (50 mL)
  6. washThe resulting solution was washed with brine (3×20 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-406bae0ab31844858ff488928e1f262e
Source dataset
uspto-grants-2016_04
Patent number
US09320713B2

Reaction notes

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