Toluene → HCID 10501092, compound

HRID 1417718Notes

Reaction equation

HRID 1417718 reaction equation
[CH3:1][O:2][C:3]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:22]([Cl:41])(C1C=CC=CC=1)(C1C=CC=CC=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.OCC1C=CC(CCl)=CC=1.C1(C)C=CC=CC=1>Cl.CCCCCCC>[C:16]1([C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:2][CH2:1][C:26]2[CH:27]=[CH:28][C:23]([CH2:22][Cl:41])=[CH:24][CH:25]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6456Trityl chlorideHCID 136388Methyl trityl etherHCID 5107660[4-(Chloromethyl)phenyl]methanol

Product 1

HCID 10501092HCID 10501092, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8900HeptaneSolvent

Procedure

A 100 mL round bottom flask was charged with triphenylmethyl methyl ether (2.74 g, 10 mmol), trityl chloride (2.79 g, 10 mmol), p-hydroxymethylbenzyl chloride (3.13 g, 20 mmol), toluene (12 mL), heptane (12 mL) and 32% HCl (2 drops). The solution was heated to reflux and 12 mL solvent was distilled over 2 hours. The solution was cooled to room temperature and the resulting slurry diluted with 12 mL heptane. After cooling in an ice bath, the product was isolated by vacuum filtration and dried in vacuo at 40° C. to give 6.27 g (79% yield) of crude product. Recrystallization from 20 mL acetonitrile gave 5.46 g (88% recovery) of the desired product. The product had a melting point of 126°-128° C. 1H NMR spectral data were as follows: (CDCl3, 300 MHz): δ 7.6-7.2 (complex, 19 H), 4.6 (s, 2H), 4.2 (s, 2H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. distillation12 mL solvent was distilled over 2 hours
  4. additionthe resulting slurry diluted with 12 mL heptane
  5. temperatureAfter cooling in an ice bath
  6. customthe product was isolated by vacuum filtration
  7. customdried in vacuo at 40° C.
  8. customto give 6.27 g (79% yield) of crude product
  9. customRecrystallization from 20 mL acetonitrile

Sources & evidence

ORD record
ord-781fd16d3253403ba5766bc0428cbdbf
Source dataset
uspto-grants-1999_03
Patent number
US05877312

Reaction notes

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