Oxalyl chloride → HCID 54541172, compound

HRID 495342Notes

Reaction equation

HRID 495342 reaction equation
[C:1]([O:12][CH2:13][CH2:14][CH:15]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH3:16])(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([O-])=[O:5].C(Cl)(=O)C(Cl)=O.[BH4-].[Na+].OS([O-])(=O)=O.[K+]>CO>[OH:5][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([O:12][CH2:13][CH2:14][CH:15]([CH3:16])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[O:11]

Participants

6

Reactant 4

HCID 65578Oxalyl chlorideHCID 516920Potassium bisulfateHCID 4311764Sodium borohydrideHCID 85701945HCID 85701945, compound

Product 1

HCID 54541172HCID 54541172, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 g (16.4 mmol) monocitronellyl (+)-phthalate was heated at reflux in 25 ml oxalyl chloride (18 eq.) for 3 h. The excess oxalyl chloride was distilled under vacuum. 5.3 g crude acid chloride was then diluted in 40 ml THF cooled to −8° under argon, and 1.87 g (3 eq.) NaBH4 was added. The reaction mixture was maintained under stirring at 0° for 4 h, then at ambient temperature for 16 h. The reaction mixture was then cooled again to 0°, and then 10 ml methanol was added dropwise. After 15 min, the mixture was poured over cold 5% KHSO4 then extracted using cold ethyl acetate. Chromatography of the crude product over silica gel (9:1 toluene/ether) yielded 1.41 g (31%) of almost pure 3,7-dimethyl-6-octenyl 2-hydroxymethylbenzoate in the form of a colourless oil.

Workup

  1. distillationThe excess oxalyl chloride was distilled under vacuum
  2. addition5.3 g crude acid chloride was then diluted in 40 ml THF
  3. temperaturecooled to −8° under argon
  4. temperatureThe reaction mixture was maintained
  5. waitat ambient temperature for 16 h
  6. temperatureThe reaction mixture was then cooled again to 0°
  7. waitAfter 15 min
  8. extractionthen extracted

Sources & evidence

ORD record
ord-b01585afe92541ebb44fb1aeec6c2965
Source dataset
uspto-grants-2005_09
Patent number
US06939835B2

Reaction notes

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