Ammonium Chloride → (4-Benzyloxy-2,6-dichloro-phenyl)methanol

HRID 2427464Notes

Reaction equation

HRID 2427464 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[C:6]([Cl:18])[C:3]=1[CH:4]=[O:5].[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[C:6]([Cl:18])[C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 111502104-(Benzyloxy)-2,6-dichlorobenzaldehyde

Product 1

HCID 66621751(4-Benzyloxy-2,6-dichloro-phenyl)methanolYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Treat a 0° C. mixture of 2,6-dichloro-4-benzyloxy-benzaldehyde (245 g, 0.871 mol) in ethanol (3 L) with sodium borohydride (32.97 g, 0.897 mol). Warm the reaction to room temperature and stir for 2 hours. Add the reaction mixture to saturated ammonium chloride (8 L). Extract the mixture with CH2Cl2 and dry the organic layer with Na2SO4. Remove the solvent in vacuo to afford 247 g (100%) of the titled product. 1H NMR (400 MHz, DMSO-d6) δ 7.38 (m, 4H), 7.33 (m, 1H), 7.12 (s, 2H), 5.14 (s, 2H), 5.05 (t, 1H), 4.59 (d, 2H).

Workup

  1. additionTreat a 0° C.
  2. temperatureWarm
  3. customthe reaction to room temperature
  4. extractionExtract the mixture with CH2Cl2
  5. dry with materialdry the organic layer with Na2SO4
  6. customRemove the solvent in vacuo

Sources & evidence

ORD record
ord-76c1dc7f15f74eac8410a11a7351d371
Source dataset
uspto-grants-2011_06
Patent number
US07968585B2

Reaction notes

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