Formaldehyde → Chloromethyl hexanoate

HRID 1866484Notes

Reaction equation

HRID 1866484 reaction equation
S(Cl)(Cl)=O.[C:5]([OH:12])(=[O:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:13]([Cl:20])(=O)CCCCC.C=O>>[C:5]([O:12][CH2:13][Cl:20])(=[O:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 8892Hexanoic AcidHCID 24386Thionyl ChlorideHCID 67340Hexanoyl chloride

Product 1

HCID 525229Chloromethyl hexanoate

Conditions

Temperature
70 °C

Procedure

Thionyl chloride (14.27 g, 0.12 mmol) was added dropwise to hexanoic acid (11.61 g, 0.10 mmol) and the reaction mixture was heated at 70° C. for 24 hours. The reaction mixture containing hexanoyl chloride was not further purified and paraformaldehyde (3.60 g, 0.12 mol) was added and the reaction mixture heated at 120° C. until the latter disappeared (about 2 hours). The reaction mixture was distilled in vacuo and chloromethyl hexanoate was obtained as a colourless oil (b.p. 118° C., 25 mbar). 1H-NMR (CDCl3) δ 5.67 (s, 2H), 2.37-2.29 (m, 2H), 1.65-1.58 (m, 2H), 1.31-1.26 (m, 4H), 0.88 (t, 3H). 13C-NMR(CDCl3) δ 179.89, 171.77, 68.53, 33.95, 31.18, 24.34, 22.26, 13.83.

Workup

  1. customwas not further purified
  2. temperaturethe reaction mixture heated at 120° C. until the
  3. custom(about 2 hours)
  4. distillationThe reaction mixture was distilled in vacuo

Sources & evidence

ORD record
ord-171f8f8aa54645e89b34df45eadd0bf8
Source dataset
uspto-grants-2009_12
Patent number
US07629383B2

Reaction notes

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