Acetic Acid → HCID 14574130, compound

HRID 2352140Notes

Reaction equation

HRID 2352140 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=CC=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:14][C:15]([OH:17])=[O:16].C[OH:19]>[Rh]>[CH2:1]([CH:7]([CH2:12][CH2:11][C:10]([OH:13])=[O:19])[CH2:14][C:15]([OH:17])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 171324-n-Hexylphenol

Product 1

HCID 14574130HCID 14574130, compound

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

A stirred suspension of 4-n-hexylphenol (972 g; 5.46 mol), 61.7 g of 5% rhodium on carbon catalyst (46.0 g of Alfa Chemical Co. lot 063081 and 17.7 g of MCB Chemicals lot A12M04), HOAc (21 ml), and MeOH (5.0 L) was hydrogenated in a 5 gallon autoclave (100 psi) at 35°-55° until 73% of theoretical H2 was consumed. A sample was withdrawn and NMR and GC tests showed that a small amount of the hexylphenol remained. Hydrogenation was continued until a total of 78% of theoretical H2 was consumed. The catalyst was filtered off, and the clear filtrate was concentrated in vacuo to a clear oil, 1065 g (106%); IR (neat) cm-1 3400, (OH) 1715 (carbonyl); NMR (CDCl3) no aromatic absorbance was observed.

Workup

  1. customwas hydrogenated in a 5 gallon autoclave (100 psi) at 35°-55° until 73% of theoretical H2
  2. customwas consumed
  3. customA sample was withdrawn
  4. customwas consumed
  5. filtrationThe catalyst was filtered off
  6. concentrationthe clear filtrate was concentrated in vacuo to a clear oil, 1065 g (106%)

Sources & evidence

ORD record
ord-d10a0e714671478e9be119592d2764fe
Source dataset
uspto-grants-1989_10
Patent number
US04876046

Reaction notes

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