Methanol → HCID 82929149, compound

HRID 575936Notes

Reaction equation

HRID 575936 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[C:6]([CH:9]=1)[CH:7]=[O:8].CO.[BH4-].[Na+]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[C:6]([CH2:7][OH:8])[CH:9]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 82926311HCID 82926311, compound

Product 1

HCID 82929149HCID 82929149, compound

Procedure

A solution of 5-Chloro-2-(2-ethyl-butoxy)-benzaldehyde, 10, (2.83 g 11.8 mmol), MeOH (50 mL) was cooled to +5° C. under N2 atmosphere and NaBH4 (0.54 g, 14.2 mmol) was added. The mixture was allowed to warm to RT over 2 hours and the volatiles were removed in vacuo. The reaction mixture was partitioned between water and CH2Cl2. The organic layer was washed with sat. brine, dried (Na2SO4) and evaporated to dryness to give 2.61 g of 5-chloro-2-(2-ethyl-butoxy)-phenyl]-methanol, 11 as a pale yellow oil.

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe reaction mixture was partitioned between water and CH2Cl2
  3. washThe organic layer was washed with sat. brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-037e8ccdc8744935b933b57bfbec4ecc
Source dataset
uspto-grants-2015_05
Patent number
US09035071B2

Reaction notes

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