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

HRID 435780Notes

Reaction equation

HRID 435780 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 one 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-5db090211beb439c9181f8b2b1da84d8
Source dataset
uspto-grants-1977_02
Patent number
US04006188

Reaction notes

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