HCID 20491272, compound → HCID 20491277, compound

HRID 2286138Notes

Reaction equation

HRID 2286138 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH:5]=[C:4]([CH3:14])[C:3]=1[OH:15].[H][H]>[Pt]=O.C(O)(=O)C>[CH3:1][CH:2]1[CH:7]([CH3:8])[CH:6]([CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:5][CH:4]([CH3:14])[CH:3]1[OH:15]

Participants

5

Reactant 2

HCID 20491272HCID 20491272, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20491277HCID 20491277, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2,3,6-trimethyl-4-(3-methyl-2-butenyl)phenol (30 g, 0.15 mol), platinum oxide (3 g), and acetic acid (150 mL) was hydrogenated at 50° C. and 200-300 psig until hydrogen uptake ceased. The mixture was filtered to remove the catalyst and the filtrate poured into water. The product was extracted with ethyl acetate and the extract washed successively with water, 5% sodium bicarbonate solution, and brine. The organic layer was dried, the solvent removed, and the residue fractionated to afford 17 g of the desired alcohol, bp 105°-110° C. (1 mm). NMR (CDCl3) δ0.7-2.2 (27H, complex pattern), 3.6 (1H, bs). IR (film) 3700, 1500, 1020, 970 cm-1. MS (m/e) 212 (M+), 123, 35, 69, 95.

Workup

  1. customwas hydrogenated at 50° C.
  2. filtrationThe mixture was filtered
  3. customto remove the catalyst
  4. additionthe filtrate poured into water
  5. extractionThe product was extracted with ethyl acetate
  6. washthe extract washed successively with water, 5% sodium bicarbonate solution, and brine
  7. customThe organic layer was dried
  8. customthe solvent removed

Sources & evidence

ORD record
ord-d4fb02ade902410890cb8679db9b8a6a
Source dataset
uspto-grants-1982_04
Patent number
US04326997

Reaction notes

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