Neopentyl alcohol → 1,1-Bis-(2,2-dimethylpropoxy)-propan-2-one

HRID 20400

Reaction equation

[CH3:1][O:2][CH:3]([O:7][CH3:8])[C:4](=[O:6])[CH3:5].C(O)[C:10]([CH3:13])([CH3:12])[CH3:11]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:11][C:10]([CH3:13])([CH3:12])[CH2:1][O:2][CH:3]([O:7][CH2:8][C:10]([CH3:13])([CH3:12])[CH3:11])[C:4](=[O:6])[CH3:5]

Participants

Conditions

Temperature: 80 °C

Procedure

Add p-toluenesulfonic acid hydrate (1.21 g, 10.58 mmol) to 1,1-dimethoxy-propan-2-one (25.00 g, 211.63 mmol) and neopentyl alcohol (46.64 g, 529.08 mmol) at room temperature. Heat in an open flask in an 80° C. oil bath for 8 hours. Allow to cool to room temperature and stir over the weekend. Purify (silica gel chromatography, eluting with 0:100 to 8:92 ethyl acetate:hexanes) to give the desired compound as a colorless oil (32.78 g 67.2%)

Workup

temperatureAllow to cool to room temperature
customPurify
wash(silica gel chromatography, eluting with 0:100 to 8:92 ethyl acetate:hexanes)

Sources & evidence

ORD record: ord-91aa903b4a07429497e2bc7b6f8efa12
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745438B2

Linked notes

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