Water → 3-(4-Tert-butyl-cyclohexyloxy)-1-methyl-naphthalene

HRID 2404198Notes

Reaction equation

HRID 2404198 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([OH:12])[CH:3]=1.[C:13]([CH:17]1[CH2:22][CH2:21][CH:20](OS(C)(=O)=O)[CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(O)(C)C.CC(=O)CC.CCOCC>[C:13]([CH:17]1[CH2:22][CH2:21][CH:20]([O:12][C:4]2[CH:3]=[C:2]([CH3:1])[C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11128255Methanesulfonic acid 4-tert-butyl-cyclohexyl esterHCID 125809284-Methylnaphthalen-2-ol

Product 1

HCID 681727973-(4-Tert-butyl-cyclohexyloxy)-1-methyl-naphthaleneYield 48.8%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6386tert-ButanolSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-methyl-naphthalen-2-ol (0.60 g, 3.8 mmol), methanesulfonic acid 4-tert-butyl-cyclohexyl ester (1.9 g, 7.6 mmol) and cesium carbonate (3.7 g, 11 mmol) in t-BuOH (10 mL) and 2-butanone (7 mL) was heated at 80° C. overnight. After cooled to room temperature, the mixture was treated with water and ether. The organic phase was dried over MgSO4, filtered and concentrated. The crude was treated with methanol to give solid product (0.55 g, yield: 48%). ESI-MS: 297.20 (M+H)+.

Workup

  1. temperatureAfter cooled to room temperature
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe crude was treated with methanol

Sources & evidence

ORD record
ord-282cd8774d5a43658a784d9384a51f01
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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