2-Methyl-6-phenoxy-hexanoic acid → 1-Hydroxy-2-methyl-6-phenoxyhexane

HRID 839835Notes

Reaction equation

HRID 839835 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3](O)=[O:4].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC.C1COCC1>[OH:4][CH2:3][CH:2]([CH3:1])[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 203221352-Methyl-6-phenoxy-hexanoic acidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 203221341-Hydroxy-2-methyl-6-phenoxyhexane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 129 g of 2-methyl-6-phenoxy-hexanoic acid in 200 ml of absolute ether and 100 ml of absolute THF was added dropwise, under exclusion of humidity, to 32 g (0.84 mol) of LiAlH4 in 1.2 l of absolute ether. After reflux and stirring for 5 hours the LiAlH4 in excess was destroyed with acetic acid and then destroyed by dropwise addition of water and a 10% sulfuric acid. The organic layer was washed with saturated NaHCO3 -solution, dried and evaporated. The crude product was immediately further reacted.

Workup

  1. temperatureAfter reflux
  2. customin excess was destroyed with acetic acid
  3. customdestroyed by dropwise addition of water
  4. washThe organic layer was washed with saturated NaHCO3 -solution
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-a1a2e789c34a402389309368378d93e7
Source dataset
uspto-grants-1978_06
Patent number
US04097496

Reaction notes

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