Sodium Hydroxide → Tert-butyl (cis-3-methoxymethoxycyclohexylmethoxy)acetate

HRID 854641Notes

Reaction equation

HRID 854641 reaction equation
[CH3:1][O:2][CH2:3][O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([CH2:11][OH:12])[CH2:6]1.[C:13]([O:17][C:18](=[O:21])[CH2:19]Br)([CH3:16])([CH3:15])[CH3:14].[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][C@@H:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([CH2:11][O:12][CH2:19][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:21])[CH2:6]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 69240471(cis-3-Methoxymethoxycyclohexyl)methanol

Product 1

HCID 69244811Tert-butyl (cis-3-methoxymethoxycyclohexylmethoxy)acetateYield 66.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

1.0 g of (cis-3-methoxymethoxycyclohexyl)methanol and 3.3 g of tert-butylbromoacetate are dissolved in 30 ml of toluene, and 0.50 g of tetrabutylammonium hydrogensulfate is added. The suspension is cooled to 10° C. 10 ml of 50% strength NaOH are added to the suspension. The mixture is allowed to warm to room temperature, and after 3 h the aqueous phase is 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 1.10 g of tert-butyl (cis-3-methoxymethoxycyclohexylmethoxy)acetate as a colorless oil. C15H28O5 (288), LCMS(ESI): 306 (M++H2O).

Workup

  1. temperatureto warm to room temperature
  2. customafter 3 h the aqueous phase is removed
  3. extractionextracted with methyl tert-butyl ether
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b2320a418093451db36f792190bfcde6
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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