Carbon Dioxide → 4-Isopropyl-2-(methoxymethoxy)benzyl Alcohol

HRID 1787920Notes

Reaction equation

[CH:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[C:6]([O:13][CH2:14][O:15][CH3:16])[CH:5]=1)([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+].C(=O)=O>O1CCCC1.CO>[CH:1]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][OH:9])=[C:6]([O:13][CH2:14][O:15][CH3:16])[CH:5]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of 4-isopropyl-2-(methoxymethoxy)benzoic acid, which may be prepared as described in Exmple 6-B, (2.40 g, 11.0 mmol) and 4-methylmorpholine (1.18 mL, 11.0 mmol) in 50 mL dry tetrahydrofuran at −10° C. was added dropwise ethyl chloroformate (1.02 mL, 11.0 mmol). After stirring at −10° C. for 20 min, sodium borohydride (1.21 g, 33.0 mmol) was added all at once. Methanol (150 mL) was cautiously added dropwise. Once the vigorous evolution of carbon dioxide had significantly decreased, the remaining methanol was added. Stirring was continued for 30 min, and the reaction was quenched with 10% acetic acid in water. The volatile solvents were removed, and the remaining material was diluted with ether. The ether was extracted with saturated NaHCO3 (2×), water (2×), brine (1×), and dried over MgSO4. The crude material was purified by chromatography over silica, using an eluent gradient of 10-30% ethyl acetate in hexanes, to afford the alcohol (1.16 g, 50%).

Workup

stirringStirring
waitwas continued for 30 min
customthe reaction was quenched with 10% acetic acid in water
customThe volatile solvents were removed
additionthe remaining material was diluted with ether
extractionThe ether was extracted with saturated NaHCO3 (2×), water (2×), brine (1×)
dry with materialdried over MgSO4
customThe crude material was purified by chromatography over silica

Sources & evidence

ORD record: ord-dff22854df074758802314edeec71394
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511066B2

Reaction notes

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