Hydrochloric Acid → Benzyl 3-hydroxy-15-methylhexadecanoate

HRID 1872807Notes

Reaction equation

HRID 1872807 reaction equation
[CH3:1][CH:2]([CH3:27])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:26])[CH2:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].[BH4-].[Na+].C(OCC)(=O)C.Cl>CC(O)C>[OH:26][CH:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]([CH3:27])[CH3:1])[CH2:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 18687298Benzyl 15-methyl-3-oxohexadecanoate

Product 1

HCID 18687221Benzyl 3-hydroxy-15-methylhexadecanoateYield 55.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzyl 15-methyl-3-oxohexadecanoate (3.74 g) in 2-propanol (50 ml) was added sodium borohydride (0.38 g) at 0° C. The mixture was stirred at 0° C. for 2 hours and poured into a mixture of ethyl acetate and diluted hydrochloric acid. The organic layer was washed with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on a silica gel column eluting with a mixture of n-hexane and ethyl acetate (10:1) to give benzyl 3-hydroxy-15-methylhexadecanoate as a colorless oil (2.10 g).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe residue was chromatographed on a silica gel column
  5. washeluting with a mixture of n-hexane and ethyl acetate (10:1)

Sources & evidence

ORD record
ord-97b8de44e41242c0a4e5ec9e86c4b291
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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