Thionyl Chloride → HCID 86054793, compound
Reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[C:11]([OH:13])=O)[O:4][CH2:3][CH2:2]1.C[O-].[Na+].S(Cl)([Cl:19])=O>CO.C1(C)C=CC=CC=1>[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[C:11]([Cl:19])=[O:13])[O:4][CH2:3][CH2:2]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
To a solution of 1,4-dioxa-spiro[4.5]decane-6-carboxylic acid (2.42 g, 13 mmol) in methanol (6 mL) was added a 5.4 N solution of sodium methoxide in methanol (2.41 mL). The mixture was stirred at 20° C. for 20 min and the solvent was then evaporated under reduced pressure. Toluene (20 mL) was added to the residue and the solvent was evaporated under reduced pressure. The white solid obtained (2.5 g) was suspended in toluene (13 mL) and thionyl chloride (1 mL, 13.8 mmol) was added to the stirred solution at 20° C. over 10 min. Stirring was continued at 40° C. for 1 h when gas evolution stopped to give a ca 1 M solution of 1,4-dioxa-spiro[4.5]decane-6-carbonyl chloride in toluene.
Workup
- customthe solvent was then evaporated under reduced pressure
- additionToluene (20 mL) was added to the residue
- customthe solvent was evaporated under reduced pressure
- customThe white solid obtained (2.5 g)
- stirringStirring
- waitwas continued at 40° C. for 1 h
Sources & evidence
- ORD record
- ord-7a4df1a880a44d709c8e648d8f903897
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07923450B2
Reaction notes
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