Water → 13-Hydroxy-oxacyclohexadecan-2-one

HRID 1109253Notes

Reaction equation

HRID 1109253 reaction equation
[O:1]=[C:2]1[CH2:18][CH2:17][CH2:16][O:15][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[BH4-].[Na+].O>CO>[OH:1][CH:2]1[CH2:18][CH2:17][CH2:16][O:15][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 3094320Oxacyclohexadecane-2,13-dioneHCID 4311764Sodium borohydride

Product 1

HCID 309431913-Hydroxy-oxacyclohexadecan-2-oneYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 480 g (1.89 mol) of 12-oxo-15-pentadecanolide (VI) in 735 ml of methanol is cooled to 10°-15° C. 26.2 g of sodium borohydride are added in portions at this temperature. The mixture is allowed to after-react at 15° C. for a further 2 hours. After addition of water, excess methanol is distilled off. The organic content of the reaction mixture is extracted with toluene, the toluene phase is washed neutral and dried, the toluene is stripped off and the residue is subjected to fractional distillation. 470 g (1.85 mol) of 12-hydroxy-15-pentadecanolide are obtained;

Workup

  1. customto after-react at 15° C. for a further 2 hours
  2. distillationis distilled off
  3. extractionThe organic content of the reaction mixture is extracted with toluene
  4. washthe toluene phase is washed neutral
  5. customdried
  6. distillationthe residue is subjected to fractional distillation

Sources & evidence

ORD record
ord-faf361481b5844578c7a42b295b98d0a
Source dataset
uspto-grants-1994_06
Patent number
US05319104

Reaction notes

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