Sodium Hydroxide → Tert-butyl [cis-3-(methoxymethoxymethyl)cyclohexylmethoxy]acetate

HRID 854659Notes

Reaction equation

HRID 854659 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][C@@H:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([CH2:12][OH:13])[CH2:7]1.Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[OH-].[Na+]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][CH2:3][O:4][CH2:5][C@@H:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([CH2:12][O:13][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 69243775(cis-3-Methoxymethoxymethylcyclohexyl)methanol

Product 1

HCID 86597946Tert-butyl [cis-3-(methoxymethoxymethyl)cyclohexylmethoxy]acetateYield 84.1%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

1.65 g of (cis-3-methoxymethoxymethylcyclohexyl)methanol and 5.1 g of tert-butyl bromoacetate are dissolved in 20 ml of toluene, and 1.50 g of tetrabutylammonium hydrogensulfate are added. The suspension is cooled to 10° C. 20 ml of 50% NaOH are added to the suspension. The mixture is stirred at 10° C. for 6 h and the aqueous phase is then removed and extracted with methyl tert-butyl ether. The combined organic phases are dried over MgSO4 and concentrated. Flash column chromatography on silica gel (heptane/ethyl acetate 10/1→2/1) gives 2.23 g of tert-butyl [cis-3-(methoxymethoxymethyl)cyclohexylmethoxy]acetate as a colorless oil.

Workup

  1. customthe aqueous phase is then removed
  2. extractionextracted with methyl tert-butyl ether
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2adfe9df57374e5886dba6a8ec5fb244
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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