Water → Benzenemethanol,2-hydroxy-3,5-dimethyl-

반응식

BrCCCC[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-:11].[Na+].[CH:13](O)([CH3:15])[CH3:14].[OH2:17].[CH3:18]CCCCC>>[OH:11][CH2:14][C:13]1[CH:15]=[C:9]([CH3:10])[CH:8]=[C:7]([CH3:6])[C:18]=1[OH:17]

참가 물질

반응물 5

HCID 962Water

HCID 3776Isopropanol

HCID 8058Hexane

HCID 127421-Bromononane

HCID 14798Sodium Hydroxide

생성물 1

HCID 11480550Benzenemethanol,2-hydroxy-3,5-dimethyl-수율 50.5%

실험 절차

A 250-mL round-bottom flask equipped with a magnetic stirrer, condenser, and Ar-inlet tube was charged with 22.0 g (145 mmol) of crude (1), 24.7 mL (130 mmol) of 1-bromononane (Fluka), 5.79 (145 mmol) of sodium hydroxide (Fisher), and 100 mL of isopropanol (Fisher). After the mixture was refluxed overnight, 100 mL of water and 100 mL of hexane (Fisher) were added. The hexane layer was washed with 20 mL of 1N NaOH (Fisher). The combined aqueous layers were extracted with 50 mL of hexane. Then, the combined hexane solutions were extracted with 100 mL+2×50 mL=200 mL of 95% methanol. The combined methanol extracts were concentrated. The residual water was removed azeotropically with 100 mL of toluene. The residue was dried at 50° C. under high vacuum to give 28.1 g of crude (2) as a brown oil; 50.5% yield from (1), 77.7% yield based on 1-bromononane.