Trichloroacetic Acid → 5-Methoxy-2,6-dimethylheptan-1-ol

HRID 1439268Notes

Reaction equation

HRID 1439268 reaction equation
C[O:2][CH:3](OC)[CH:4]([CH3:13])[CH2:5][CH2:6][CH:7]([O:11][CH3:12])[CH:8]([CH3:10])[CH3:9].ClC(Cl)(Cl)C(O)=O.[OH-].[Na+].[BH4-].[Na+]>CO.O.O1CCCC1>[OH:2][CH2:3][CH:4]([CH3:13])[CH2:5][CH2:6][CH:7]([O:11][CH3:12])[CH:8]([CH3:9])[CH3:10]

Participants

8

Reactant 4

HCID 6421Trichloroacetic AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 213990641,1,5-Trimethoxy-2,6-dimethylheptane

Product 1

HCID 213991185-Methoxy-2,6-dimethylheptan-1-ol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.9 g. of 1,1,5-trimethoxy-2,6-dimethylheptane in 200 ml. of tetrahydrofuran and 60 ml. of water is treated with one g. of trichloroacetic acid and then the mixture heated at 60° for 1 hour. After cooling, there is added 40 ml. of 2N sodium hydroxide in methanol followed by 2 g. of powdered sodium borohydride. The reaction mixture is stirred at room temperature for three hours and then concentrated and extracted with ether. The ethereal extracts are evaporated under reduced pressure to give crude 1-hydroxy-5-methoxy-2,6-dimethylheptane which can be purified by distillation.

Workup

  1. temperatureAfter cooling
  2. additionthere is added 40 ml
  3. concentrationconcentrated
  4. extractionextracted with ether
  5. customThe ethereal extracts are evaporated under reduced pressure

Sources & evidence

ORD record
ord-8b7bb32dfb134d5698f5c6a6df1f9da8
Source dataset
uspto-grants-1977_11
Patent number
US04058666

Reaction notes

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