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5-(2'-Hydroxy-3',4',6'-trimethylbenzoyl)pentanoic acid → 6-Hydroxy-6-(2'-hydroxy-3',4',6'-trimethylphenyl)hexanoic acid

HRID 1248599
Notes
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Reaction equation

HRID 1248599 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C:8]1[C:22]([CH3:23])=[C:21]([CH3:24])[CH:20]=[C:19]([CH3:25])[C:9]=1[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:11]>O1CCCC1>[OH:11][CH:10]([C:9]1[C:19]([CH3:25])=[CH:20][C:21]([CH3:24])=[C:22]([CH3:23])[C:8]=1[OH:7])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 129061485-(2'-Hydroxy-3',4',6'-trimethylbenzoyl)pentanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 129061466-Hydroxy-6-(2'-hydroxy-3',4',6'-trimethylphenyl)hexanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a well stirred suspension of lithium aluminum hydride (2 parts) in dry tetrahydrofuran (50 volume parts) was added a solution of 5-(2'-hydroxy-3',4',6'-trimethylbenzoyl)pentanoic acid (formula II-1 wherein R=H3C, X=H, Y=OH, n=4, in the free form) in dry tetrahydrofuran (10 volume parts) at room temperature. After being stirred under reflux for 2 hours, the mixture was cooled to 0° C., acidified with cold dilute hydrochlororic acid, and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residue was subjected to column chromatography on silica gel and eluted with carbon tetrachloride-acetone (5:1). From the 1st fraction, 6-hydroxy-6-(2'-hydroxy-3',4',6'-trimethylphenyl)hexanoic acid (formula II-3 wherein R=H3C, X=H, Y=OH, n=4, in the free form) (0.45 part) was obtained as colorless needles melting at 165°-166° C.

Workup

  1. customat room temperature
  2. stirringAfter being stirred
  3. temperatureunder reflux for 2 hours
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. washeluted with carbon tetrachloride-acetone (5:1)

Sources & evidence

ORD record
ord-9e4dcff56fac4062a6c96cd093660417
Source dataset
uspto-grants-1985_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04525361

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes