HCID 12906128, compound → HCID 12906145, compound

HRID 1390572Notes

Reaction equation

HRID 1390572 reaction equation
[OH:1][C:2]1[C:18]([CH3:19])=[C:17]([CH3:20])[CH:16]=[C:15]([CH3:21])[C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10](OCC)=[O:11])=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:1][C:2]1[C:18]([CH3:19])=[C:17]([CH3:20])[CH:16]=[C:15]([CH3:21])[C:3]=1[CH:4]([OH:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11]

Participants

4

Reactant 2

HCID 12906128HCID 12906128, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12906145HCID 12906145, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 5-(2'-hydroxy-3',4',6'-trimethylbenzoyl)pentanoate (formula II-1 wherein R=H3C, X=H, Y=OH, n=4, in the form of ethyl ester) (0.4 part) in tetrahydrofuran (100 volume parts) was reduced with lithium aluminum hydride (0.5 part) under warming for 1 hour. The reaction mixture was quenched with ethyl acetate followed by the addition of saturated aqueous sodium sulfate (5 volume parts) solution. After removal of the resulting inorganic salt by filtration, the filtrate was condensed in vacuo to dryness. The residue was crystallized from diethyl ether to give 1-(2'-hydroxy-3',4',6'-trimethylphenyl)-1,6-hexanediol (formula III-3 wherein R=H3C, X=H, Y=OH, n=4, in the free form) (0.32 part) as colorless needles melting at 135°-136° C.

Workup

  1. temperatureunder warming for 1 hour
  2. customThe reaction mixture was quenched with ethyl acetate
  3. additionfollowed by the addition of saturated aqueous sodium sulfate (5 volume parts) solution
  4. customAfter removal of the resulting inorganic salt
  5. filtrationby filtration
  6. customcondensed in vacuo to dryness
  7. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-37b8650b862442ef9ad42de6991827c1
Source dataset
uspto-grants-1979_02
Patent number
US04139545

Reaction notes

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