Water → HCID 20090614, compound

HRID 275185Notes

Reaction equation

HRID 275185 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].Cl[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:19]([CH3:24])([CH3:23])[CH2:18][CH2:17][C:16]([CH3:26])([CH3:25])[C:15]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O.[I-].[Na+]>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:19]([CH3:24])([CH3:23])[CH2:18][CH2:17][C:16]([CH3:26])([CH3:25])[C:15]=2[CH:14]=1)[CH:5]=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 28008916-(Chloromethyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 20090614HCID 20090614, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 180AcetoneSolvent

Procedure

3,4-Dihydroxybenzaldehyde (0.580 g., 4.20 mmol, 1 equiv.) is dissolved in 4.2 mL of acetone. 2-Chloromethyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene) (18a) (1.00 g., 4.20 mmol, 1 equiv.), sodium iodide (0.020 g., 0.133 mmol, 0.03 equiv.), and potassium carbonate (0.580 g., 4.20 mmol, 1 equiv.) are added, and the mixture is heated to reflux for 19 hours. The mixture is poured into water, and extracted twice with ether, and once with EtOAc. The combined extracts are washed with brine, dried (MgSO4), and concentrated. The crude material is chromatographed on silica gel using EtOAc/hexane as the eluent to afford 3-hydroxy-4-[5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl]methoxy benzaldehyde (41) (0.666 g., 1.97 mmol, 47%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 9.87 (s, 1H, CHO), 7.48-7.35 (m, 4H, ArH), 7.22 (dd, J= 2, 8 Hz, 1H, ArH), 7.09 (d, J=8 Hz, 1H, ArH), 5.14 (s, 2H, ArCH2O), 1.72 (s, 4H, CH2CH2), 1.32 (s, 6H, 2×CH3), 1.31 (s, 6H, 2×CH3); 13C NMR (75 MHz, CDCl3) δ 191.00 (C=0), 151.20, 146.33, 145.79, 145.53, 132.11, 130.76, 127.17, 126.53, 125.51, 124.31, 114.28, 111.42, 71.60, 34.92, 34.26, 31.82; IR (KBr) 3342, 2962, 2932, 1682, 1608, 1582, 1512, 1278, 1112 cm-1 ; MS (DCI) m/e 339 (MH+), 201 (C15H21+).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 19 hours
  3. extractionextracted twice with ether
  4. washThe combined extracts are washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude material is chromatographed on silica gel

Sources & evidence

ORD record
ord-007ad2788f264a4ca81e78bf0afdeebc
Source dataset
uspto-grants-1995_02
Patent number
US05391817

Reaction notes

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