Sodium borohydride → Tert-butyl 3-hydroxyoctadecanoate

HRID 236474Notes

Reaction equation

HRID 236474 reaction equation
[O:1]=[C:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[BH4-].[Na+]>CO>[OH:1][CH:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 16110963Tert-butyl 3-oxooctadecanoate

Product 1

HCID 13962663Tert-butyl 3-hydroxyoctadecanoateYield 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 3-oxooctadecanoate (130 g) in methanol (700 ml) was added sodium borohydride (15 g) at 0° C. in a portionwise. The mixture was stirred for 1 hour at 0° C. To the reaction mixture was added ice water and from this whole the object compound was extracted with ethyl acetate. The ethyl acetate solution was washed with water, dried over magnesium sulfate and then evaporated to give a residue which was dried up by using high vacuum pump to afford crude tert-butyl 3-hydroxyoctadecanoate (126.6 g) as an oil.

Workup

  1. extractionfrom this whole the object compound was extracted with ethyl acetate
  2. washThe ethyl acetate solution was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give a residue which
  6. customwas dried up

Sources & evidence

ORD record
ord-cb6f234fc8bd413b9c61f0f659d9cb06
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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