HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Hydroxide → Ethyl 8-acetyl-12-hydroxy-12-methylheptadecanoate

HRID 372897
Notes
Print preview

Reaction equation

HRID 372897 reaction equation
[C:1]([CH:4]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:3])[CH3:2].[OH-:26].[Na+].[BH4-].[Na+]>O.O1CCCC1>[C:1]([CH:4]([CH2:16][CH2:17][CH2:18][C:19]([OH:26])([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 4311764Sodium borohydrideHCID 54103623HCID 54103623, compound

Product 1

HCID 20322206Ethyl 8-acetyl-12-hydroxy-12-methylheptadecanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

Mercuric acetate (3.8 g., 0.012 mole) is dissolved in water (12 ml.) and tetrahydrofuran (20 ml.) is added to give a suspension of a yellow solid. Then, ethyl 8-acetyl-12-methyl-11-heptadecenoate (4.2 g., 0.012 mole) in tetrahydrofuran (20 ml.) is added, and the mixture stirred at room temperature for 24 hours. After 6 hours, the yellow suspended solid has disappeared and a cloudy solution results. To the solution is added 3M sodium hydroxide solution (12 ml.), followed by 0.5M sodium borohydride solution is 3M sodium hydroxide (12 ml.). Liquids are decanted from the precipitated mercury. The organic layer is taken up in ether, washed with three portions of water and dried over sodium sulfate. Evaporation of the ether leaves 4.4 g. of ethyl 8-acetyl-12-hydroxy-12-methylheptadecanoate as a yellowish oil used in the next step without further purification; pmr (CDCl3) δ 0.88 (3H,t), 1.13 (3H,s, CH3COH), 1.25 (3H,t, CH3CH2OCO--), 2.12 (3H,s, CH3CO), 4.12 (2H,q).

Workup

  1. customto give
  2. additiona suspension of a yellow solid
  3. waitAfter 6 hours
  4. customa cloudy solution results
  5. customLiquids are decanted from the precipitated mercury
  6. washwashed with three portions of water
  7. dry with materialdried over sodium sulfate
  8. customEvaporation of the ether
  9. customleaves 4.4 g
  10. customof ethyl 8-acetyl-12-hydroxy-12-methylheptadecanoate as a yellowish oil used in the next step without further purification

Sources & evidence

ORD record
ord-6e553390d5e141868426a7068e310da1
Source dataset
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04092356

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes