Methanol → HCID 14586596, compound

HRID 1872801Notes

Reaction equation

HRID 1872801 reaction equation
S(Cl)(Cl)=O.[OH:5][CH:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:7]([OH:9])=[O:8].[CH3:23]O>>[OH:5][CH:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:7]([O:9][CH3:23])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 52829032-Hydroxypentadecanoic acid

Product 1

HCID 14586596HCID 14586596, compound

Conditions

Temperature
0 °C

Procedure

To methanol (10 ml), cooled in an ice-brine bath, was added thionyl chloride (0.87 ml) dropwise. After stirring at 0° C. for 10 minutes, 2-hydroxypentadecanoic acid (1.54 g) was added. The mixture was stirred at room temperature for 3 hours, and concentrated under vacuum. The residue was dissolved in ethyl acetate (60 ml), and washed with water (40 ml×2), saturated aqueous sodium bicarbonate (30 ml), and brine (30 ml). The organic phase was dried, concentrated to dryness, and triturated in diisopropyl ether to give methyl 2-hydroxypentadecanoate (0.77 g).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate (60 ml)
  4. washwashed with water (40 ml×2), saturated aqueous sodium bicarbonate (30 ml), and brine (30 ml)
  5. customThe organic phase was dried
  6. concentrationconcentrated to dryness
  7. customtriturated in diisopropyl ether

Sources & evidence

ORD record
ord-c7249b4867fc4855a7da209ce6e298f7
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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