Methyl Chloride → HCID 53801387, compound

HRID 918302Notes

Reaction equation

HRID 918302 reaction equation
[CH2:1]([C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([OH:15])[C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22]Cl>CN(C)C=O>[CH2:1]([C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([O:15][CH3:22])[C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6327Methyl ChlorideHCID 54410738HCID 54410738, compound

Product 1

HCID 53801387HCID 53801387, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Into a suspension of 0.75 g of 66% sodium hydride-paraffin in 20 cc of dimethylformamide was added a solution of 5.6 g of allyl α-benzyl-α-hydroxyphenylacetate in 10 cc of dimethylformamide under cooling, and the mixture was stirred for 1 hour. Successively, methyl chloride was introduced into the mixture. The reaction mixture was poured in ice-water and the resultant was subjected to extraction with ether. The ether extract was washed with an aqueous solution saturated with sodium chloride, and dried over sodium sulfate. Thereafter, ether was distilled out and paraffin was removed, whereby, 5.1 g oily allyl α-benzyl-α-methoxyphenylacetate, nD25 1.5488 was obtained.

Workup

  1. temperatureunder cooling
  2. extractionthe resultant was subjected to extraction with ether
  3. extractionThe ether extract
  4. washwas washed with an aqueous solution saturated with sodium chloride
  5. dry with materialdried over sodium sulfate
  6. distillationThereafter, ether was distilled out and paraffin
  7. customwas removed

Sources & evidence

ORD record
ord-ef9b0cdaeee342b6875e0026eb65d940
Source dataset
uspto-grants-1976_07
Patent number
US03970703

Reaction notes

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