Heptane → 4-(Benzyloxy)-3-(propan-2-yl)phenol

HRID 1609733Notes

Reaction equation

HRID 1609733 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([CH:19]([CH3:21])[CH3:20])[CH:6]=1)(=O)C.[OH-].[Na+].CCCCCCC>O.CO>[CH2:12]([O:11][C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][C:7]=1[CH:19]([CH3:21])[CH3:20])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 8900HeptaneHCID 14798Sodium HydroxideHCID 19030080HCID 19030080, compound

Product 1

HCID 190301014-(Benzyloxy)-3-(propan-2-yl)phenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-Benzyloxy-3-isopropylphenyl acetate (5.59 kg, 19.7 mol) is added to a solution of sodium hydroxide (1.20 kg, 30.0 mol) in a mixture of water (30 L) and methanol (30 L). This solution is stirred at 24° for 1 hour. A black-colored solution develops. This is concentrated in vacuo (40°, 3 Torr) to remove the methanol. This residue is then extracted with ethyl acetate (2×16 L) and the combined organic layers are washed with aqueous sodium hydroxide (1 N, 2×10 L) and water (3×12 L). The solvent is stripped in vacuo (50°, 3 Torr) to yield an amber oil. This oil is then trimmed with heptane (10 L) for 4 hours and the allowed to stand overnight at room temperature at which time the solids are collected by filtration and washed with cold heptane (2×1 L). After air-drying, the product is further dried in vacuo (25°, 120 Torr) for 72 hours to give 4-benzyloxy-3-isopropylphenol as a low melting solid, m.p. 39°-40°.

Workup

  1. concentrationThis is concentrated in vacuo (40°, 3 Torr)
  2. customto remove the methanol
  3. extractionThis residue is then extracted with ethyl acetate (2×16 L)
  4. washthe combined organic layers are washed with aqueous sodium hydroxide (1 N, 2×10 L) and water (3×12 L)
  5. customis stripped in vacuo (50°, 3 Torr)
  6. customto yield an amber oil
  7. waitto stand overnight at room temperature at which time
  8. filtrationthe solids are collected by filtration
  9. washwashed with cold heptane (2×1 L)
  10. customAfter air-drying
  11. customthe product is further dried in vacuo (25°, 120 Torr) for 72 hours

Sources & evidence

ORD record
ord-4fb60e8b702048378c5a58c65a82258a
Source dataset
uspto-grants-1995_03
Patent number
US05401772

Reaction notes

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