Methanol → Methyl 16-hydroxyhexadecanoate

HRID 2260070Notes

Reaction equation

HRID 2260070 reaction equation
[C:1]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][OH:20]>C[O-].[Na+]>[OH:20][CH2:19][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:17][CH3:16])=[O:18]

Participants

4

Reactant 2

HCID 887MethanolHCID 7984Hexadecanolide

Product 1

HCID 3496888Methyl 16-hydroxyhexadecanoateYield 90.2%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideCatalyst

Conditions

Temperature
60 °C

Procedure

76.3 gm of 16-hexadecanolide and 0.29 gm of 28% sodium methoxide solution were dissolved into 250 gm of methanol, and the solution was heated at 60° C. for 60 hours while stirring. The reaction mixture was cooled to deposit crystals. The crystals were collected by filtration, washed, and dried to obtain 77.5 gm of methyl 16-hydroxyhexadecanoate (yield: 90.2%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe crystals were collected by filtration
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-04f7a6b5e03e4850a90d567fac551a1e
Source dataset
uspto-grants-1995_12
Patent number
US05476649

Reaction notes

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