p-Toluenesulfonic acid → (4,4-Dimethoxy-cyclohexyloxymethyl)-benzene

HRID 1948141Notes

Reaction equation

HRID 1948141 reaction equation
[CH:1]([O:6][CH3:7])([O:4][CH3:5])OC.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:19]([O:26][CH:27]1[CH2:32][CH2:31]C(=O)[CH2:29][CH2:28]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)(O)[O-].[Na+]>CO.ClCCl>[CH3:7][O:6][C:1]1([O:4][CH3:5])[CH2:29][CH2:28][CH:27]([O:26][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 109873694-(Benzyloxy)cyclohexanone

Product 1

HCID 10988715(4,4-Dimethoxy-cyclohexyloxymethyl)-benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

529 mL of trimethyl orthoformate and 32 mg of p-toluene sulfonic acid were added to a solution of 4-benzyloxy cyclohexanone in 20 mL of dry methanol and the mixture was stirred overnight. 20 mL of saturated aqueous sodium bicarbonate solution and 20 mL of dichloromethane were added, the aqueous layer was extracted several times with dichloromethane and the combined organic layers were dried and evaporated to dryness to yield 1.50 g of the desired product, which was used without further purification.

Workup

  1. extractionthe aqueous layer was extracted several times with dichloromethane
  2. customthe combined organic layers were dried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-8f3f32b2e5e74c94b7c63c93ec610db1
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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