Methanol → HCID 560328, compound

HRID 1197743Notes

Reaction equation

[CH3:1][CH:2]([CH2:6][CH:7]([CH3:10])[CH2:8][CH3:9])[C:3]([OH:5])=[O:4].S(Cl)(Cl)=O.[CH3:15]O>>[CH3:1][CH:2]([CH2:6][CH:7]([CH3:10])[CH2:8][CH3:9])[C:3]([O:5][CH3:15])=[O:4]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 391772,4-Dimethylhexanoic acid

Product 1

HCID 560328HCID 560328, compound

Procedure

The product of part (i) above (385 mg) in methanol (10 ml) was treated dropwise with thionyl chloride 0.4 ml, 5.5 mmol) at 0° C. and then the solution was stood at room temperature overnight. The excess methanol was removed by distillation at atmospheric pressure, and the residue was distilled to give the title compound (216 mg), [α]19 +33° (liquid, 1=0.1 dm, d22 =0.871), lit1 [α]23 +D D 32.2° (liquid 1=0.2 dm), υmax (CHBr3) 1725 cm-1 (ester), δ(CDCl3) 3.67 (s, 3H, CO2CH3), 2.57 (m, 1H, CH2CHCH2), 1.33 and 1.13 (m, 1H each, CH2CH3), 1.16 (d, J7 Hz, 3H, C--2H3), 0.89 (d, J7 Hz, 3H, C--4CH3), 0.87 (t, J7 Hz, 3H, CH2CH3) lit2 (NMR spectrum).

Workup

customThe excess methanol was removed by distillation at atmospheric pressure
distillationthe residue was distilled

Sources & evidence

ORD record: ord-bc3178c0023644f78eaf3a880300df7c
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05278067

Reaction notes

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